Methanol → HCID 13826023, compound

HRID 1709288Notes

Reaction equation

HRID 1709288 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO.[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:21][CH:22]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 13826007HCID 13826007, compound

Product 1

HCID 13826023HCID 13826023, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.4 g. (29.8 mmole) 4-Bromobenzenesulphonic acid(4-acetylphenethylamide) are dissolved in a mixture of 40 ml. methanol and 100 ml. ethanol and 0.85 g. (22.4 mmole) sodium borohydride then added portionwise thereto at 0° C. Subsequently, the reaction mixture is stirred at ambient temperature for 2 hours and then evaporated in a vacuum. After the addition of dilute hydrochloric acid, the reaction mixture is shaken out with methylene chloride and the methylene chloride phase is dried with anhydrous sodium sulphate Thereafter, it is evaporated and the residue is recrystallised from toluene. Yield 10.4 g. (91% of theory): m.p. 125°-127° C.

Workup

  1. customat 0° C
  2. customevaporated in a vacuum
  3. additionAfter the addition of dilute hydrochloric acid
  4. stirringthe reaction mixture is shaken out with methylene chloride
  5. dry with materialthe methylene chloride phase is dried with anhydrous sodium sulphate
  6. customit is evaporated
  7. customthe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-95fda55b648342a59791b51be1304dcd
Source dataset
uspto-grants-1990_08
Patent number
US04948809

Reaction notes

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