4-Bromo-3-methylaniline → HCID 772005, compound

HRID 1708061Notes

Reaction equation

HRID 1708061 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:14].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:9][C:8]=1[CH3:14]

Participants

5

Reactant 3

HCID 233594-Bromo-3-methylanilineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 772005HCID 772005, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.88 ml) was added dropwise to a stirred solution of 4-bromo-3-methylbenzenamine (1.02 g) in pyridine (9 ml) under nitrogen at -10° to -14° C. After 2 h, aqueous (8%) sodium bicarbonate (35.6 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined, dried organic extracts were evaporated and the residue crystallized from ethyl acetate to give the title compound as a white powder (100 mg). The mother liquors were evaporated onto silica gel (Merck 7734, 3 ml) and the residue applied as a plug to a flash column of silica gel (Merck 9385). Elution with hexane:ethyl acetate (85:15) afforded a further sample of the title compound as a white solid (250 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  2. customdried organic extracts were evaporated
  3. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-72f2aefc554544a4b30a612c01ebcbc8
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

Loading…