Ethyl 4-bromobutyrate → HCID 53945522, compound

HRID 1395126Notes

Reaction equation

HRID 1395126 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]Br)[CH3:2].[Cl:10][C:11]1[CH:21]=[CH:20][C:14]([CH2:15][NH:16][C:17](=[S:19])[S-:18])=[CH:13][CH:12]=1.[NH4+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][S:19][C:17](=[S:18])[NH:16][CH2:15][C:14]1[CH:20]=[CH:21][C:11]([Cl:10])=[CH:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 15811499HCID 15811499, compound

Product 1

HCID 53945522HCID 53945522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 160 g. of 4-bromobutyric acid ethyl ester in 1125 ml. of absolute dimethylformamide were added gradually under an atmosphere of argon at 0° C. while stirring well and cooling, 172.3 g. of ammonium (N-4-chlorobenzyl)dithiocarbamate, the temperature was maintained constant. The slightly yellow solution was stirred overnight at room temperature, diluted with 1500 ml. of water and extracted four times with 500 ml. of ethyl acetate each time. The combined organic phases were washed three times with 200 ml of saturated sodium chloride solution each time and dried over 80 g. of magnesium sulfate with the addition of carbon, filtered and evaporated under reduced pressure. The resulting crystalline residue was recrystallized from 700 ml. of diisopropyl ether, and 218 g. of 4-{[(p-chlorobenzyl)thiocarbamoyl]thio}-butyric acid ethyl ester having a melting point of 61°-62° C. was obtained.

Workup

  1. temperaturecooling
  2. stirringThe slightly yellow solution was stirred overnight at room temperature
  3. additiondiluted with 1500 ml
  4. extractionof water and extracted four times with 500 ml
  5. washThe combined organic phases were washed three times with 200 ml of saturated sodium chloride solution each time
  6. customdried over 80 g
  7. additionof magnesium sulfate with the addition of carbon
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe resulting crystalline residue was recrystallized from 700 ml

Sources & evidence

ORD record
ord-9f11677ecf6e44e8902dcd8cce300dbd
Source dataset
uspto-grants-1980_05
Patent number
US04202832

Reaction notes

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