Acetic Acid → HCID 19817708, compound

HRID 1087230Notes

Reaction equation

HRID 1087230 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:5]=1[C:6]([C:8]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:9]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[O:7].C(O)(=O)C.O>O1CCCC1>[F:3][C:4]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:5]=1[CH:6]([C:8]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:9]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[OH:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 19817721HCID 19817721, compound

Product 1

HCID 19817708HCID 19817708, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (1.49 g) was added portionwise to a stirred mixture of 2'-(2,4-difluorobenzoyl)-4'-nitromethanesulfonanilide (5.6 g) in tetrahydrofuran (50 ml). The mixture was stirred at room temperature for 4 hours, treated with acetic acid (5 ml) and water (20 ml), had concentrated to dryness. The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried and evaporated to give a powder of 2'-(2,4-difluoro-α-hydroxybenzyl)-4'-nitromethanesulfonanilide (5.3 g).

Workup

  1. concentrationhad concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-15ec34e55bc449079f99daa7f4be1427
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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