2,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene → HCID 86743152, compound

HRID 1904872Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

7.32 g (0.24 mmole) of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene are dissolved in 30 ml of dimethylsulfoxide and then a solution of 3.75 g (20 mmoles) of 5-amino-4,6-dimethylthiopyrimidine in 20 ml of dimethylsulfoxide and a solution of 2.69 g of potassium tert-butylate in 20 ml of dimethylsulfoxide are added simultaneously dropwise at 15° C. with cooling. The reaction solution is stirred for 15 hours at 20° C. and then poured into ice-water and, after neutralisation with acetic acid, extracted three times with chloroform. The extracts are washed with water, dried over sodium sulfate, and the chloroform is removed, affording 10.7 g of a yellow oil. The crude product is purified by chromatography through a solumn of silica gel, affording 2.04 g of starting 5-amino-4,6-di(methylmercapto)pyrimidine and 2.8 g of a yellow product which is recrystallised from 1 ml of toluene and 5 ml of cyclohexane to give 2.03 g of compound 1.2 of m.p. 146°-147° C.

Workup

temperaturewith cooling
extractionafter neutralisation with acetic acid, extracted three times with chloroform
washThe extracts are washed with water
dry with materialdried over sodium sulfate
customthe chloroform is removed

Sources & evidence

ORD record: ord-e7f0522ee21c4ff59ecb0555f1f97a02
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04840662

Reaction notes

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