Water → 5-chloro-N-chlorocarbonyl-N-{2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethyl}-6-methyl-4-pyrimidine amine

HRID 1460956Notes

Reaction equation

ClC([O:4][C:5]([Cl:8])(Cl)Cl)=O.[Cl:9][C:10]1[C:11]([NH:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])=[CH:23][C:22]=2[CH3:32])=[N:12][CH:13]=[N:14][C:15]=1[CH3:16].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[Cl:9][C:10]1[C:11]([N:17]([C:5]([Cl:8])=[O:4])[CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])=[CH:23][C:22]=2[CH3:32])=[N:12][CH:13]=[N:14][C:15]=1[CH3:16]

Participants

Conditions

Temperature: 5 °C

Procedure

An amount 2.0 g of trichloromethyl chloroformate (TCF) was dissolved in 30 ml of toluene and cooled to 5° C. or lower. To the solution was added dropwise a solution of 5.0 g of 5-chloro-N-{2-[4-(2-ethoxyethyl)2-methylphenoxy]ethyl}-6-methyl-4-pyrimidine amine and 1.8 g of triethylamine dissolved in 20 ml of toluene, and after the dropwise addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 20 ml of water was added, and the mixture was stirred at room temperature for one hour to decompose excessive TCF.

Workup

additionafter the dropwise addition
additionwas added
stirringthe mixture was stirred at room temperature for one hour

Sources & evidence

ORD record: ord-b466e75864cb470e90716710c97d6197
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073558

Reaction notes

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