Water → HCID 178473548, compound

HRID 2399031Notes

Reaction equation

HRID 2399031 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.[CH2:8]([S:10][C:11](=[NH:13])[NH2:12])[CH3:9].O.[OH-].[Na+]>C(Cl)Cl.C(#N)C>[CH2:5]([O:4][C:2]([NH:12][C:11]([NH2:13])=[SH:10][CH2:8][CH3:9])=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide3×HCID 9877395HCID 9877395, compound

Product 1

HCID 178473548HCID 178473548, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

302 g. (2.78 moles) of ethyl chloroformate was added to 2 moles of S-ethylisothiourea hydrochloride in 800 ml. of water and 200 ml. of acetonitrile. A 25% solution of sodium hydroxide was added dropwise so rapidly that, with external cooling, a temperature of +25° C. was not exceeded. The solution of sodium hydroxide was added for as long as the pH value did not rise above 8. Stirring was effected for a further 80 minutes during which control of the pH value was continued. If necessary, a little more solution of sodium hydroxide was added. A two phase system, aqueous and organic, resulted. The product was isolated from the organic phase by extraction with methylene chloride and concentration in vacuo to a light yellow oil.

Workup

  1. customa temperature of +25° C.
  2. customA two phase system, aqueous and organic, resulted

Sources & evidence

ORD record
ord-552e7b2064db4faa99996d7777062066
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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