Hydrochloric Acid → HCID 13105762, compound

HRID 1632494Notes

Reaction equation

HRID 1632494 reaction equation
[O:1]=[C:2]1[CH2:8][O:7][CH:6]([C:9]2C=[CH:13][CH:12]=[CH:11][C:10]=2C(F)(F)F)[C:5]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:4]=2[NH:3]1.[BH4-].[Na+].Cl.C[N:28](C)C=O>>[O:1]=[C:2]1[CH2:8][O:7][CH:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:28]=2)[C:5]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:4]=2[NH:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 13068343HCID 13068343, compound

Product 1

HCID 13105762HCID 13105762, compound

Procedure

To a solution of Compound 2 (9.8 g) in dimethylformamide (80 ml) is gradually added sodium borohydride (1.1 g) at 0° C., and the mixture is stirred at the same temperature for 2 hours, mixed with ice water, acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue is purified on column chromatography [silica gel/methylene chloride-ethyl acetate (20:3 v/v)] to give crystalline 2-(2-chloroacetyl)amino-2'-trifluoromethylbenzohydrol (4.8 g), which is recrystallized from ether-n-hexane to give pure crystals of Compound 3, mp. 116°-117° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified on column chromatography [silica gel/methylene chloride-ethyl acetate (20:3 v/v)]
  7. customto give crystalline 2-(2-chloroacetyl)amino-2'-trifluoromethylbenzohydrol (4.8 g), which
  8. customis recrystallized from ether-n-hexane

Sources & evidence

ORD record
ord-d0ee3e2a432f4b5db04c73d9b50b5b36
Source dataset
uspto-grants-1984_10
Patent number
US04476133

Reaction notes

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