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Acetic Acid → 2'-(2,4-Difluorophenylamino)-4'-(1-hydroxyethyl)methanesulfonanilide

HRID 1087209
Notes
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Reaction equation

HRID 1087209 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:16]=[CH:15][C:9]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:8]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:8]1[CH:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:16]=[CH:15][C:9]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10472404HCID 10472404, compound

Product 1

HCID 198177352'-(2,4-Difluorophenylamino)-4'-(1-hydroxyethyl)methanesulfonanilideYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.2 g) was added portionwise to a solution of 4'-acetyl-2'-(2,4-difluorophenylamino)methanesulfonanilide (1.5 g) in methanol (15 ml) at 5° to 10° C. The mixture was stirred for 10 hours at room temperature, treated with acetic acid, and concentrated. The residue was triturated with water and filtered. The solid (1.6 g) was recrystallized from a mixture of ethanol and ethyl acetate to give colorless needles of 2'-(2,4-difluorophenylamino)-4'-(1-hydroxyethyl)methanesulfonanilide (0.89 g).

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with water
  3. filtrationfiltered
  4. customThe solid (1.6 g) was recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-c6c7c42167474d90a4a3265dfdc17545
Source dataset
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05034417

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes