Acetyl chloride → HCID 18463642, compound

HRID 2231125Notes

Reaction equation

HRID 2231125 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2[NH:17][C:16]([C:18]([F:21])([F:20])[F:19])=[N:15][C:14]=2[C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:9]=[C:10]([CH3:12])[CH:11]=1.C(N(CC)CC)C>C(#N)C>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2[N:17]([C:1](=[O:3])[CH3:2])[C:16]([C:18]([F:21])([F:19])[F:20])=[N:15][C:14]=2[C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:26][CH:27]=2)[CH:9]=[C:10]([CH3:12])[CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178426113HCID 178426113, compound

Product 1

HCID 18463642HCID 18463642, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetyl chloride (50 mg, 0.6 mmol) was added to a cold (5° C.), stirred solution of Example 54 (150 mg, 0.3 mmol) and triethylamine (80 mg, 0.8 mmol) in acetonitrile (3 ml). The reaction was warmed to room temperature and stirred for 4 hours. The solvent was removed and the residue was purified by chromatography on silica gel using 20% ethyl acetate in toluene as the eluent to give 15 mg of the desired product as a crystalline solid: mp 257° C. Anal. Calc'd. for C20H16N2O3ClF3S (MW 456.87): C, 52.58; H, 3.53; N, 6.13; S, 7.02. Found: C, 52.21; H, 3.61; N, 5.95; S, 7.30.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by chromatography on silica gel using 20% ethyl acetate in toluene as the eluent

Sources & evidence

ORD record
ord-49380fd492324009b6fd8bab93b15e8a
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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