Acetyl chloride → HCID 22287249, compound

HRID 2301056Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:25])[C:18]([O:21][C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19].C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].C(OCC)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:33](=[O:35])[CH3:34])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:25])[C:18]([O:21][C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 2.5 °C

Procedure

N-[2-Chloro-4-(4-aminophenylsulphanyl)phenyl]-2-acetoxy-2-methylpropanamide (Method 22) (0.50 g) was dissolved in DCM (10 ml) and cooled to 0-5° C. in an ice bath. Triethylamine (0.46 ml) was added followed by dropwise addition of acetyl chloride (0.1 ml) and the mixture was allowed to warm to ambient temperature over 2 hours. Ethyl acetate (20 ml) was added and the solution was washed with water (2×10 ml) and brine then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 40-80% ethyl acetate/hexane to give the title compound (0.470 g) as a solid. NMR (CDCl3): 1.8 (s, 6H), 2.2 (d, 6H), 7.2-7.3 (m, 5H), 7.5 (d, 2H), 8.3 (d, 1H), 8.4 (s, 1H); MS (ESP−): 419; EA: found: C, 56.7; H, 5.0; N, 6.0%; C20H21ClN2O4S.0.4 EtOAc requires C, 56.9; H, 5.3; N, 6.1%.

Workup

temperatureto warm to ambient temperature over 2 hours
washthe solution was washed with water (2×10 ml) and brine
customthen dried
customVolatile material was removed by evaporation
customthe residue was purified by flash chromatography
washeluting with 40-80% ethyl acetate/hexane

Sources & evidence

ORD record: ord-da636010a47740e9ae23cbe33f234b5e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498275B1

Reaction notes

Loading…