Water → HCID 15790727, compound

HRID 1276219Notes

Reaction equation

HRID 1276219 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[NH2:12][CH:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=1)[CH2:14][CH2:15][OH:16].C(N(CC)CC)C.O>C(#N)C>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH:13]([NH:12][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=2[F:11])[CH2:14][CH2:15][OH:16])=[CH:22][CH:21]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 15790734HCID 15790734, compound

Product 1

HCID 15790727HCID 15790727, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,6-Difluorobenzoyl chloride (2.65 g, 0.015 mol) is added in portions to a solution of 3-amino-3- (4-t-butylphenyl)-1-propanol (3.1 g, 0.015 mol) and triethylamine (3.03 g, 0.04 mol) in 30 ml of acetonitrile at room temperature (20° C.) in the course of 10 minutes. The reaction mixture is further stirred for 7 hours, water is added and the mixture is extracted with ethyl acetate. 4.5 g of N-[1-(4-t-butylphenyl)-3-hydroxy-propyl]-2,6-difluorobenzamide are isolated from the ethyl acetate phase as a crude product having a content of 28% according to GC/MS analysis, which is employed as such in the next reaction step.

Workup

  1. extractionthe mixture is extracted with ethyl acetate

Sources & evidence

ORD record
ord-aa8aafef7a274e3c9616bbcb5332ef76
Source dataset
uspto-grants-2000_12
Patent number
US06166010

Reaction notes

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