4-Cyanobenzoyl chloride → HCID 24759617, compound

HRID 1967654Notes

Reaction equation

HRID 1967654 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[N:29]([CH3:31])[CH3:30])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH3:25])=[O:6].C(=O)(O)[O-].[Na+].[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)#[N:38]>C(OCC)(=O)C>[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43]([NH:1][C:2]2[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=2[N:29]([CH3:31])[CH3:30])[C:5]([NH:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])=[CH:10][C:9]=2[CH3:25])=[O:6])=[O:44])=[CH:41][CH:40]=1)#[N:38]

Participants

5

Reactant 3

HCID 801724-Cyanobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 59202372HCID 59202372, compound

Product 1

HCID 24759617HCID 24759617, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-4-dimethylamino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (200 mg, 0.44 mmol) (see Example I9) was dissolved in a biphasic mixture of ethyl acetate (4 ml) and aqueous sodium bicarbonate (1N) (4 ml). 4-Cyano-benzoyl chloride (75 mg, 0.44 mmol) was added under vigorous stirring. The reaction mixture was stirred for 18 hours at ambient temperature. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. Purification by chromatography over silica gel (eluent:cyclohexane/ethyl acetate ratio 1:1) gave Compound No. A16 of Table A below (244 mg, 95% yield).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by chromatography over silica gel (eluent:cyclohexane/ethyl acetate ratio 1:1)
  5. customgave Compound No

Sources & evidence

ORD record
ord-71221166bace475396f504c5ac264885
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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