Acetyl chloride → HCID 388025, compound

HRID 566453Notes

Reaction equation

HRID 566453 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH:6]([C:8]1[S:12][C:11]2[C:13](=[O:21])[C:14]3[CH:18]=[CH:17][S:16][C:15]=3[C:19](=[O:20])[C:10]=2[CH:9]=1)[CH3:7]>ClCCCl>[C:1]([O:5][CH:6]([C:8]1[S:12][C:11]2[C:13](=[O:21])[C:14]3[CH:18]=[CH:17][S:16][C:15]=3[C:19](=[O:20])[C:10]=2[CH:9]=1)[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 388024HCID 388024, compound

Product 1

HCID 388025HCID 388025, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Acetyl chloride (1.1 g, 13.6 mmol) was added to a solution of 10 (2.0 g, 7.4 mmol) in 1,2-dichloroethane (100 mL) and the mixture was refluxed for 4 h. After this time, the solution was poured into ice water. The organic layer was separated, washed with saturated NaHCO3 and water, dried, and evaporated. The residue was subjected to column chromatography (silica gel, C6H6) to give 11 as a yellow solid (mp 174-176° C.) in a 74% yield: IR (KBr) 1645, 1655, 1724 (C═O) cm−1; 1H NMR (CDCl3) δ 1.68 (d, J=6.6 Hz, 3H, CHCH3), 2.13 (s, 3H, COCH3), 6.10-6.17 (q, J=6.6 Hz, 1H, CH), 7.53 (s, 1H, H-3), 7.63 (d, J=5.1 Hz, 1H, H-7), 7.68 (d, J=5.1 Hz, 1H, H-6); 13C NMR (CDC3): δ 21.0 (C-2-COCH3), 22.0 (C-2-CHCH3), 67.4 (C-2-CH), 123.4 (C-3), 126.6 (C-7), 133.6 (C-6), 154.0 (C-2), 169.8 (C-2-C═O), 174.4×2 (C-4, C-8); MS m/z 306 (M+); Anal. (C14H10O4S2) C, H.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a6226e98524c4cd4a68166596c923806
Source dataset
uspto-grants-2001_01
Patent number
US06174913B1

Reaction notes

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