Bromine → HCID 22418352, compound
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]#[N:15])[C:11]([S:16][C:17]([F:20])([F:19])[F:18])=[C:10]2[NH2:21])=[CH:5][CH:4]=1.[Br:24]Br>ClCCl.CCCCCC>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([Br:24])=[C:12]([C:14]#[N:15])[C:11]([S:16][C:17]([F:19])([F:20])[F:18])=[C:10]2[NH2:21])=[CH:5][CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1.17 g (3.30 mmoles) of 1-(4-trifluoromethylphenyl)-2-amino-3-trifluoromethylthio-4-cyanopyrrole and 0.46 ml (0.34 g, 3.3 mmoles) of triethylamine in 20 ml of chloroform cooled to -20° C. was added a solution of 0.19 ml (0.59 g, 3.7 mmoles) of bromine in 5 ml of chloroform. The reaction mixture was stirred at -20° C. for 1 hour and then allowed to warm to 0° C. Another 0.04 ml (0.13 g, 0.8 mmole) of bromine was then added and after 15 minutes of additional stirring, the reaction mixture was diluted with dichloromethane and partitioned with water and a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give 1.11 g of a brown solid. This material was combined with that from a previous reaction of 1.00 g (2.8 mmoles) of 1-(4-trifluoromethylphenyl)- 2-amino-3-trifluoromethylthio-4-cyanopyrrole and 0.15 ml of bromine. Chromatography on silica gel eluting with 3:1 v/v dichloromethane-hexane furnished 1.40 g (52%) of 1-(4-trifluoromethylphenyl)-2-amino-3-trifluoromethylthio-4-cyano-5-bromopyrrole (EXAMPLE 14A) as a yellow solid. Recrystallization from hexane-ethyl acetate provided the product as light yellow platelets, melting point about 175° C.
Sources & evidence
- ORD record
- ord-f7bd06721b1a40a787a6f4324bf5f8c9
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05187185
Reaction notes
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