2,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene → HCID 86743153, compound

HRID 1904873Notes

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]([Cl:28])=[N:22][C:23]([CH3:27])=[N:24][C:25]=1[Cl:26].CC([O-])(C)C.[K+]>O1CCCC1>[Cl:15][C:4]1[C:3]([N+:16]([O-:18])=[O:17])=[C:2]([N:24]2[C:25]([Cl:26])=[C:20]([NH2:19])[C:21]([Cl:28])=[N:22][CH:23]2[CH3:27])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12]

Participants

Conditions

Temperature: -30 °C

Procedure

6.71 g (0.022 mole) of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene and 3.56 g (0.020 mole) of 5-amino-4,6-dichloro-2-methylpyrimidine are dissolved in 50 ml of tetrahydrofuran. The solution is cooled to -30° C. and, at this temperature, a solution of 4.6 g (0.041 mole) of potassium tert-butylate in 50 ml of tetrahydrofuran is added dropwise. After 1 hour at -30° to 0° C., the mixture is extracted with water and ethyl acetate while adding 10 ml of acetic acid. The extracts are dried over sodium sulfate and concentrated, affording 10.5 g of an oil as crude product. This product is purified by chromatography through a column of silica gel using a mixture of 3 parts of petroleum ether and 1 part of ethyl acetate. The solvent is removed by rotary evaporation, affording 8.3 g of product as residue. Recrystallisation from a mixture of toluene and cyclohexane yields 6.80 g (69.2% of theory) of yellow crystals with a melting point of 134°-136° C.

Workup

extractionthe mixture is extracted with water and ethyl acetate
additionwhile adding 10 ml of acetic acid
dry with materialThe extracts are dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-518b0f81db2740978b1bad1e8f85dcde
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04840662

Reaction notes

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