Ammonium Acetate → HCID 9975666, compound

HRID 1087227Notes

Reaction equation

HRID 1087227 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:30].[Na+]>CO>[NH2:30][CH:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 10450972Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-

Product 1

HCID 9975666HCID 9975666, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide (2.5 g), ammonium acetate (5.4 g) and sodium cyanoborohydride (0.96 g) in methanol (50 ml) was refluxed for 5 hours. The mixture was concentrated to dryness. The residue was dissolved in ethyl acetate, washed with water, dried, and evaporated. The residue (2.6 g) was purified by column chromatography on silica gel (70 g) eluting with a mixture of chloroform and methanol (9:1) to give a white powder of 4'-(1-aminoethyl)-2'-(2,4-difluorophenylthio)methanesulfonanilide (0.84 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe mixture was concentrated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue (2.6 g) was purified by column chromatography on silica gel (70 g)
  8. washeluting with a mixture of chloroform and methanol (9:1)

Sources & evidence

ORD record
ord-e11ee8f2d5264c49a871ef9f157e1570
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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