Bromine → 2-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline
Reaction equation
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(=O)(O)[O-].[Na+].[Br:25]Br>CO.C(Cl)Cl>[Br:25][C:9]1[CH:8]=[C:7]([CH2:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[CH:19]=[CH:18][C:10]=1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a chilled suspension of 4-methylaminosulfonylmethyl-N-trifluoroacetylaniline (10.9 g) in methanol (100 mL) was added sodium bicarbonate (28 g), followed by bromine (18.3 g) in methylene chloride (30 mL). The reaction mixture was then diluted with methylene chloride (70 mL) and quenched by the addition of sodium sulfite (20 g), filtered through CELITE and concentrated in vacuo to a yellow residual solid. This solid was twice reslurried in methylene chloride (300 mL) then refiltered and the filtrates evaporated in vacuo. The residual materials were combined in 10% acetone/methylene chloride solution and concentrated then purified by column chromatography (eluting with 4% acetone in methylene chloride) to give the title compound (4.10 g) mp 170° C.; TLC (methylene chloride/acetone 15:1) Rf=0.36, and the corresponding dibromide (5.56 g) TLC (methylene chloride/acetone 15:1) Rf=0.31.
Workup
- customquenched by the addition of sodium sulfite (20 g)
- filtrationfiltered through CELITE
- concentrationconcentrated in vacuo to a yellow residual solid
- customthe filtrates evaporated in vacuo
- concentrationconcentrated
- customthen purified by column chromatography (eluting with 4% acetone in methylene chloride)
Sources & evidence
- ORD record
- ord-7fd82d0668ad417c9cbc207b049337a7
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05578612
Reaction notes
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