Triethylamine → HCID 10338212, compound

HRID 1087218Notes

Reaction equation

HRID 1087218 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])=[CH:13][C:10]([C:11]#[N:12])=[C:9]([CH3:24])[CH:8]=1.C(N(CC)CC)C>N1C=CC=CC=1>[C:11]([C:10]1[C:9]([CH3:24])=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[C:14]([S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:13]=1)#[N:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10446139HCID 10446139, compound

Product 1

HCID 10338212HCID 10338212, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (2.2 ml) was added dropwise to an ice-cooled solution of 4-amino-5-(2,4-difluorophenylthio)-2-methylbenzonitrile (3.9 g) and triethylamine (3.9 ml) in pyridine (40 ml). The mixture was stirred overnight at room temperature and concentrated to dryness. To the residue were added pyridine (10 ml) and 5% aqueous solution of sodium hydroxide (50 ml). The resulting mixture was stirred for 2 hours and washed with toluene (50 ml). The aqueous layer was acidified with hydrochloric acid, and the precipitates obtained were recrystallized from a mixture of ethanol and ethyl acetate to give a pale brown powder of 4'-cyano-2'-(2,4-difluorophenylthio)-5'-methylmethanesulfonanilide (2.6 g).

Workup

  1. concentrationconcentrated to dryness
  2. additionTo the residue were added pyridine (10 ml) and 5% aqueous solution of sodium hydroxide (50 ml)
  3. stirringThe resulting mixture was stirred for 2 hours
  4. washwashed with toluene (50 ml)
  5. customthe precipitates obtained
  6. customwere recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-b3f5e76754cf4c099795ecb13ab1296f
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

Loading…