Acetyl chloride → HCID 67063052, compound

HRID 599269Notes

Reaction equation

HRID 599269 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:7]([F:20])=[CH:8][C:9]([CH3:19])=[C:10]([C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([NH:5][C:6]1[C:7]([F:20])=[CH:8][C:9]([CH3:19])=[C:10]([C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67063163HCID 67063163, compound

Product 1

HCID 67063052HCID 67063052, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (3.12 g, 40 mmol) was added to a 0° C. solution of ethyl 2-(5-amino-4-fluoro-2-methylphenyl)-2-oxoacetate (9 g, 40 mmol) and Et3N (8.1 g, 80 mmol) in CH2Cl2 (80 mL). The resulting mixture was stirred at RT for 3 h. The solvent was removed under reduced pressure to give ethyl 2-(5-acetamido-4-fluoro-2-methylphenyl)-2-oxoacetate (10.7 g, 100% yield), which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3): δ 8.71 (d, J=6.0 Hz, 1 H), 7.37 (brs, 1 H), 6.95 (d, J=8.7 Hz, 1 H), 4.39 (q, J=7.2 Hz, 2 H), 2.50 (s, 3H), 2.10 (s, 3 H), 1.40 (t, J=7.2 Hz, 3 H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-682123c968574c21bcae6b03425619f8
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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