Potassium Carbonate → N-[2-Chloro-4-(4-aminophenylsulphanyl)phenyl]-2-acetoxy-2-methylpropanamide

HRID 1062400Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[CH:11]([O:14][C:15](=[O:17])[CH3:16])[CH2:12]C.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:26][C:23]2[CH:24]=[CH:25][C:20]([NH2:19])=[CH:21][CH:22]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]([O:14][C:15](=[O:17])[CH3:16])([CH3:12])[CH3:27]

Participants

Conditions

Temperature: 135 °C

Procedure

Copper (I) chloride (0.90 g) was added to a mixture of N-[2-chloro-4-iodophenyl]-2-acetoxy-3-methylpropanamide (Method 23) (8.3 g), 4-aminothiophenol (1.07 ml) and potassium carbonate (9.1 g) in DMF (100 ml). The mixture was heated at 135° C. with stirring under argon for 3 hours, cooled and then filtered through diatomaceous earth. The filter was washed with ethyl acetate (3×20 ml) and the filtrates were combined and washed with water (50 ml), brine and dried. The volatile material was removed by evaporation. The crude product was purified by flash chromatography eluting with 20-40% ethyl acetate/hexane to give the title compound (4.99 g) as a solid. Mp 130-132° C.; NMR (CDCl3): 1.7 (s, 6H), 2.1 (s, 3H), 3.8 (s, 2H), 6.6 (d, 2H), 7.1 (m, 2H), 7.2 (m, 2H), 8.2 (d, 1H), 8.4 (s, 1H); MS (ESP−): 377.

Workup

temperaturecooled
filtrationfiltered through diatomaceous earth
washThe filter was washed with ethyl acetate (3×20 ml)
washwashed with water (50 ml), brine
customdried
customThe volatile material was removed by evaporation
customThe crude product was purified by flash chromatography
washeluting with 20-40% ethyl acetate/hexane

Sources & evidence

ORD record: ord-890e804fcb1443e998211f7e7b7813de
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960688B2

Reaction notes

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