Chloroacetyl chloride → HCID 53477038, compound

HRID 1505205Notes

Reaction equation

HRID 1505205 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH2:17])=[CH:5][CH:4]=1.Cl[CH2:24][C:25](Cl)=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9]([C:10]2[C:11]3[NH:17][C:25](=[O:26])[CH2:24][O:16][C:12]=3[CH:13]=[CH:14][CH:15]=2)=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 67424503HCID 67424503, compound

Product 1

HCID 53477038HCID 53477038, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-(trifluoromethyl)benzyl)-2-amino-3-hydroxybenzamide 22a (1 g, 3.2 mmol) was dissolved in 20 ml of DMF and at 0° C. TEA (0.9 ml, 2 equiv.) and chloroacetyl chloride (0.3 ml, 1.2 equiv.) were added. The mixture was stirred at rt for 2 hours. K2CO3 (885 mg, 2 equiv.) was added and the reaction was stirred at rt for 20 hours. The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 1/petroleum ether 1 as eluant gave 500 mg of a white solid. Yield=44% 1HNMR (DMSO, 200 MHz) δ 4.56 (2H, d, J=5.4 Hz), 4.65 (2H, s), 7.04 (2H, t), 7.17 (1H, d, J=7.8 Hz), 7.55 (2H, d, J=8 Hz), 7.71 (2H, d, J=8.2 Hz), 9.52 (1H, bs), 10.96 (1H, bs); [M+1] 351.1 (C17H13F3N2O3 requires 350.3).

Workup

  1. stirringthe reaction was stirred at rt for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude residue by chromatographic column

Sources & evidence

ORD record
ord-5865e091dd7146069ec39ac4f86a10c0
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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