Sarcosine → HCID 22662727, compound

HRID 1060534Notes

Reaction equation

HRID 1060534 reaction equation
[OH-].[Na+].Cl[S:4]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH:8]=1)(=[O:6])=[O:5].[NH:16]([CH2:18][C:19]([OH:21])=[O:20])[CH3:17].C1(C)C=CC=CC=1>O>[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([S:4]([N:16]([CH2:18][C:19]([OH:21])=[O:20])[CH3:17])(=[O:6])=[O:5])=[CH:8]1

Participants

6

Reactant 4

HCID 1088SarcosineHCID 1140TolueneHCID 14798Sodium HydroxideHCID 27763401-Benzothiophene-3-sulfonyl chloride

Product 1

HCID 22662727HCID 22662727, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

6 g of NaOH, 23.27 g of 3-chlorosulphonyl-benzothiophene and 13.36 g of sarcosine are added to a mixture of 200 ml of toluene and 200 ml of water and stirred for 6.5 hours at 60° C. For working up, the aqueous phase is separated off and the organic phase is extracted with 100 ml of 2 N NaOH solution. The combined aqueous phases are acidified with conc. HCl and then extracted twice with 300 ml of ethyl acetate. After washing with saturated aqueous saline solution and drying over magnesium sulphate the organic phase is concentrated by evaporation. The crude product obtained is recrystallised from 100 ml of dichloroethane. Yield: 13.14 g. M.p.: 139-140° C.

Workup

  1. customthe aqueous phase is separated off
  2. extractionthe organic phase is extracted with 100 ml of 2 N NaOH solution
  3. extractionextracted twice with 300 ml of ethyl acetate
  4. washAfter washing with saturated aqueous saline solution
  5. dry with materialdrying over magnesium sulphate the organic phase
  6. concentrationis concentrated by evaporation

Sources & evidence

ORD record
ord-e63a3461ef814ffcb95ef53bca701930
Source dataset
uspto-grants-2003_02
Patent number
US06525045B2

Reaction notes

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