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In 1518 a new project brought together three Sienese painters, Sodoma, Beccafumi and Girolamo del Pacchia. The new project was a scheme of fresco paintings to embellish the interior of a meeting room belonging to one of the city's oldest confraternities - the Confraternity of Santa Maria degli Angeli della Veste Nera (Saint Mary of the Angels and of the Black Robes). Founded in honour of the Virgin after 1450 the confraternity also adopted Bernardino as one of their saints, adding his name to the confraternity's title. For this reason the room that painters decorated is now known as the Oratory of San Bernardino. Designed as a place where the members of the confraternity would meet to conduct both their collective devotions and their administrative business, the Oratory of San Bernardino offers a rare example of an early sixteenth-century decorative ensemble that has survived in almost its original form.
On the side walls of the room there is a series of large-scale fresco paintings separated from one another by pilasters decorated with candelabra motifs. The paintings consist of narrative scenes from the life of the Virgin. Beccafumi had been entrusted with painting the Betrothal and the Dormition.
In Beccafumi's painting of the Betrothal of the Virgin, his preference for slender, elegant figurative types that are much less amply proportioned than those of Sodoma and Girolamo del Pacchia is apparent. The elaborately decorated marble doorway in the Betrothal of the Virgin, with its striking frieze and pilaster, together with the circular building behind it and to the left, demonstrate the painter's interest in architecture, both ancient and contemporary, which he could have seen in Rome. Indeed, the circular building bears a strong resemblance to the Tempietto, that was constructed in 1502 by the architect Bramante near the Roman church of San Pietro in Montorio.
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