Hydrochloric Acid → N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamide

HRID 2301031Notes

Reaction equation

HRID 2301031 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N:18](S(C)(=O)=O)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([O:32]C(=O)C)([CH3:31])[CH3:30].Cl.C(Cl)Cl>O.CO>[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([OH:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 22287442N-[2-Chloro-4-{4-(N,N-dimesylamino)phenylsulphanyl}phenyl]-2-acetoxy-2-methylpropanamide

Product 1

HCID 22287414N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamideYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of lithium hydroxide monohydrate (0.177 g) in water (1.8 ml) was added to a stirred solution of N-{2-chloro-4-[4-(N,N-dimesylamino)phenylsulphanyl]phenyl}-2-acetoxy-2-methylpropanamide (Method 26) (0.45 g) in methanol (3.5 ml) and the mixture was stirred at ambient temperature for 4 hours. Water (3 ml) was added and the solution was acidified to pH 2-3 with 1M hydrochloric acid. DCM (20 ml) was added and the organic layer was washed with water (20 ml) and brine, then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 30-70% ethyl acetate/hexane to give the title compound (0.30 g) as a solid. Mp 138-140° C.; NMR (CDCl3): 1.5 (s, 6H), 3.0 (s, 3H), 7.1-7.4 (m, 7H), 8.4 (d, 1H), 9.3 (s, 1H); MS (ESP−): 413; EA: found: C, 48.9; H, 4.4; N, 6.5%; C17H19ClN2O4S2 requires C, 49.2; H, 4.6; N, 6.8%.

Workup

  1. washthe organic layer was washed with water (20 ml) and brine
  2. customdried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by flash chromatography
  5. washeluting with 30-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f1948779fd3549628a717482cc224f69
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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