Benzhydrylamine → HCID 20064774, compound

HRID 359294Notes

Reaction equation

HRID 359294 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[NH2:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[C:18]1([CH:17]([NH:16][C:2]2[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 20064774HCID 20064774, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reaction vessel was charged with 120 ml of toluene and 11.0 g (42.4 mmol) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate (prepared as described in U.S. Pat. No. 4,199,506). Then, 15.5 g (86 mmol) of aminodiphenylmethane was added in one portion. The resulting yellowish-orange solution was refluxed under nitrogen for 9 days. Then, solvent was removed from the mixture under reduced pressure to yield a yellowish-orange solid material, which was flash chromatographed (~38 ml/min) on silica gel using 10% ethyl acetate in hexane solvent. There was obtained 13.2 g of a thick yellow oil which solidified upon standing to a yellow solid product (m.p.=92°-95° C.) identified in Table I.

Workup

  1. customprepared
  2. temperatureThe resulting yellowish-orange solution was refluxed under nitrogen for 9 days
  3. customThen, solvent was removed from the mixture under reduced pressure
  4. customto yield a yellowish-orange solid material, which
  5. customchromatographed (~38 ml/min) on silica gel using 10% ethyl acetate in hexane solvent

Sources & evidence

ORD record
ord-ce90dc6f8b824f0c817f2c24dc46e184
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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