Hydrochloric Acid → HCID 19771121, compound

HRID 1589874Notes

Reaction equation

HRID 1589874 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=3[NH:10][C:9]2=[O:21])[CH:7]=1.[OH-].[K+].[NH2:25]OS(O)(=O)=O.Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([F:18])([F:20])[F:19])=[CH:16][C:11]=3[N:10]([NH2:25])[C:9]2=[O:21])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 5311330HCID 5311330, compound

Product 1

HCID 19771121HCID 19771121, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-dihydro-1-(5-chloro-2-hydroxyphenyl)-5-trifluoromethyl-2H-benzimidazol-2-one (0.2 g, 0.6 mmol) in absolute N,N-dimethylformamide (5 ml) was at room temperature added potassium hydroxide (2 pellets) and hydroxylamine-o-sulfonic acid (0.16 g, 1.3 mmol) The reaction was stirred over night, water was added (20 ml) and the mixture was acidified with 4 M hydrochloric acid. The crude crystalline product was collected by filtration and subjected to column chromatography using methylene chloride:methanol (19 1) as eluent. The fractions containing the product were concentrated in vacuo yielding the title compound as white crystals, M.p. 228°-230° C.

Workup

  1. customwas at room temperature
  2. filtrationThe crude crystalline product was collected by filtration
  3. additionThe fractions containing the product
  4. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-c32fde4742874db8b2885cb74c720185
Source dataset
uspto-grants-1993_04
Patent number
US05200422

Reaction notes

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