Hydrochloric Acid → 2-Bromo-1-(4-chloro-3-sulfamoylphenyl)-ethanol

HRID 67786

Reaction equation

HRID 67786 reaction equation
C([BH3-])#N.[Na+].[Br:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([S:16](=[O:19])(=[O:18])[NH2:17])[CH:10]=1)=[O:8].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C.C(O)(=O)C>[Br:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([S:16](=[O:19])(=[O:18])[NH2:17])[CH:10]=1)[OH:8]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 12952390Bromo-4'-chloro-3'-sulfamoylacetophenone

Product 1

HCID 205271912-Bromo-1-(4-chloro-3-sulfamoylphenyl)-ethanol

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.94 g of sodium cyanoborohydride are added to an ice-cold solution of 3.1 g of 2-bromo-4'-chloro-3'-sulfamoylacetophenone and 1 ml of aqueous methyl orange solution in 20 ml of tetrahydrofuran, with stirring, and the pH is then rapidly adjusted to 3-4 by the dropwise addition of a 1:1 mixture of glacial acetic acid and 2 N HCl (indicator red in color) and the pH is then kept at this value by the occasional dropwise addition of the acid mixture. After about 11/2 hours no further starting material can be detected in a thin layer chromatogram (Merck silica gel ready-for-use plates, ethyl acetate as the solvent). The reaction mixture is poured into 300 ml of water and the resulting mixture is saturated with sodium chloride and extracted several times with ethyl acetate. After the combined organic phases have been washed with water and dried over sodium sulfate, they are concentrated in a rotary evaporator. Colorless crystals with a melting point of 145° C. (with decomposition).

Workup

  1. additionthe pH is then kept at this value by the occasional dropwise addition of the acid mixture
  2. custom2 hours no further starting material
  3. extractionextracted several times with ethyl acetate
  4. washAfter the combined organic phases have been washed with water
  5. dry with materialdried over sodium sulfate, they
  6. concentrationare concentrated in a rotary evaporator

Sources & evidence

ORD record
ord-674f7bb147564f6ab35283906948eeee
Source dataset
uspto-grants-1982_08
Patent number
US04346088

Linked notes

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