Ethyl chloroformate → HCID 54202608, compound

HRID 426431Notes

Reaction equation

HRID 426431 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([N:5]=[C:6]1[N-:10][N:9]=[C:8]([S:11][CH3:12])[S:7]1)=[O:4].[Na].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(#N)C>[CH2:19]([O:18][C:16]([N:10]1[N:9]=[C:8]([S:11][CH3:12])[S:7][C:6]1=[N:5][C:3](=[O:4])[N:2]([CH3:13])[CH3:1])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 5360545SodiumHCID 178503618HCID 178503618, compound

Product 1

HCID 54202608HCID 54202608, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

80.5 g of 2-(dimethylcarbamoylimino)-5-methylthio-1,3,4-thiadiazol-3-id, sodium salt, were suspended in 300 ml of acetonitrile and treated dropwise with stirring with 36.5 g of ethyl chloroformate at room temperature. The mixture was further stirred for 2 hours, treated with ice water, the precipitated substance separated by suction filtration, and recrystallized from acetonitrile. There is obtained 84.5 g (86.9% of theory) of 2-(dimethylcarbamoylimino)-5-methylthio-1,3,4-thiadiazolin-3-carboxylic acid ethyl ester of m. pt. 129° C.

Workup

  1. additiontreated dropwise
  2. customthe precipitated substance separated by suction filtration
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-717c82c94e04442897de762c40be3fbf
Source dataset
uspto-grants-1979_10
Patent number
US04169718

Reaction notes

Loading…