Water → HCID 12926278, compound

HRID 894510Notes

Reaction equation

HRID 894510 reaction equation
Cl[CH:2]([NH:7][C:8](=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16](=[O:18])[CH3:17])[C:3]([Cl:6])([Cl:5])[Cl:4].[CH:20]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([CH3:27])[CH:21]=1.C(N(CC)CC)C.O>CC(C)=O>[CH3:27][C:22]1[CH:21]=[CH:20][C:25]([O:26][CH:2]([NH:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16](=[O:18])[CH3:17])[C:3]([Cl:6])([Cl:5])[Cl:4])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 8471TriethylamineHCID 129224872-[(1,2,2,2-Tetrachloroethyl)carbamoyl]phenyl acetate

Product 1

HCID 12926278HCID 12926278, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15.0 g of N-(1',2',2',2'-tetrachloroethyl)-2-acetoxybenzamide and 5.65 g of p-cresol were dissolved in 250 ml of acetone. 5.3 g of triethylamine were added dropwise thereto at a temperature below 12° C. After effecting the reaction at room temperature for 30 minutes, the reaction mixture was poured into water. 15.2 g of white N-(1'-p-methylphenoxy-2',2',2'-trichloroethyl)-2-acetoxybenzamide were obtained. The compound was suspended in 300 ml of ethanol, then 3.6 ml of concentrated hydrochloric acid were added thereto and the reaction was carried out at --60°-70° C. for three hours. After cooling, the reaction mixture was poured into water to obtain 14.3 g of N-(1'-p-methylphenoxy-2',2',2'-trichloroethyl)-2-hydroxbenzamide as white crystals. M.p. 126°-127° C.

Workup

  1. customat a temperature below 12° C
  2. customthe reaction at room temperature for 30 minutes

Sources & evidence

ORD record
ord-6ddc0301a1324e60ac2967dc8bb2100b
Source dataset
uspto-grants-1981_08
Patent number
US04284628

Reaction notes

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