Chloroform → HCID 14294136, compound

HRID 1381693Notes

Reaction equation

HRID 1381693 reaction equation
[S:1]=[C:2](C(S)C(OCC)=O)[CH3:3].[NH:11]([C:13]([O:15][CH3:16])=[O:14])[NH2:12].C(Cl)(Cl)Cl.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>ClCCl>[S:1]=[C:2]([NH:12][NH:11][C:13]([O:15][CH3:16])=[O:14])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 66225Magnesium orthosilicateHCID 80519Methyl carbazateHCID 86742729HCID 86742729, compound

Product 1

HCID 14294136HCID 14294136, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 129 g of 2-(1-thioxoethyl)thioglycolic acid, ethyl ester, 67.5 g of methyl hydrazinocarboxylate and 500 ml of chloroform was heated at reflux for 8 hours, then concentrated in vacuo. The oily residue was concentrated further under high vacuum, giving a yellow oil. This oil was dissolved in 500 ml of dichloromethane and passed through a bed of hydrous magnesium silicate, washing with additional dichloromethane. The resulting light yellow oil was crystallized from toluene-methylcyclohexane, giving 70 g of the desired compound as ivory crystals, mp 99°-100.5° C. Proton nuclear magnetic resonance (δ [ppm], CDCl3) 90 MHz: 2.42 (s, 3H, CH3CS); 3.76 (s, 3H, OCH3); 8.55 (bs, 1H, NH); 9.56 (bs, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. concentrationconcentrated in vacuo
  4. concentrationThe oily residue was concentrated further under high vacuum
  5. customgiving a yellow oil
  6. washwashing with additional dichloromethane
  7. customThe resulting light yellow oil was crystallized from toluene-methylcyclohexane

Sources & evidence

ORD record
ord-c840d9e293d84dfda41a7b5dee0975f5
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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