Acetyl chloride → 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide

HRID 1789660Notes

Reaction equation

HRID 1789660 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][N:5]([C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[C:25](Cl)(=[O:27])[CH3:26].CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2][CH2:3][CH2:4][N:5]([C:16](=[O:24])[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:25](=[O:27])[CH3:26])(=[O:13])=[O:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 220362104-[(2-Methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-benzenesulfonamide

Product 1

HCID 220361694-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-benzenesulfonamide (0.32 g, 0.88 mmol), acetyl chloride (0.069 mL, 76 mg, 0.97 mmol), and Et3N (0.13 mL, 97 mg, 0.96 mmol) in CH2Cl2 (9 mL) was heated at reflux for 2 h. After cooling, the mixture was evaporated in vacuo, and the residue was purified by MPLC (CH2Cl2 to 60:40 CH2Cl2/EtOAc) to afford 0.29 g (81%) of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide as a colorless glass; 1H NMR δ 2.03 (s, 3H), 2.15 (s, 3H), 2.77 (m, 2H), 4.15 (m, 2H), 6.90 (dd, 2H, J=7.5, 7.5), 7.24 (d, 2H, J=9.0), 7.32 (dd, 2H, J=3.0, 9.0), 7.92 (d, 2H, J=9.0), 9.1 (br s, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter cooling
  3. customthe mixture was evaporated in vacuo
  4. customthe residue was purified by MPLC (CH2Cl2 to 60:40 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-4505b8678b23482e8a59f5cccef83453
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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