Hydrochloric Acid → 2-Acetylamino-N-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-acetamide

HRID 1827440Notes

Reaction equation

HRID 1827440 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][C:7]=1[F:21])=[O:4].Cl.[C:23](Cl)(=[O:25])[CH3:24].C(N(CC)CC)C>O>[C:23]([NH:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)=[CH:8][C:7]=1[F:21])=[O:4])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 104470352-amino-N-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-acetamide

Product 1

HCID 103595132-Acetylamino-N-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-N-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-acetamide (1:1) hydrochloride (50 mg, 0.15 mmol), acetyl chloride (14.4 mg, 0.18 mmol), triethylamine (31 mg, 0.30 mmol) was stirred at 0° C. for 4 h. Then the mixture was diluted with water and the mixture extracted with DCM. The organic layer was then washed with brine, dried, filtered and evaporated to leave the title compound (50 mg, 99%) as a white solid. MS: m/e=335.2 (M++H).

Workup

  1. extractionthe mixture extracted with DCM
  2. washThe organic layer was then washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-353e9f69adcb48f393b0daf847c302c8
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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