Methyl carbazate → HCID 14294118, compound

HRID 1381696Notes

Reaction equation

HRID 1381696 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](C(S)C(O)=O)=[S:10])=[CH:4][CH:3]=1.[NH:16]([C:18]([O:20][CH3:21])=[O:19])[NH2:17]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:17][NH:16][C:18]([O:20][CH3:21])=[O:19])=[S:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 19858437HCID 19858437, compound

Product 1

HCID 14294118HCID 14294118, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 37.0 g of 2-[2-(4-methylphenyl)-1-thioxoethyl]thioglycolic acid, 18.2 g of methyl hydrazinocarboxylate and 250 ml of dichloromethane was heated at reflux for one hour and then evaporated in vacuo. The residue was concentrated at high vacuum and 45° C. for one hour. The oily residue was chromatographed on a 75×800mm dry column of silica gel, eluting with dichloromethane. The desired fractions were pooled and the solid crystallized from toluene-hexane, giving 30 g of the desired compound as off-white needles, mp 104.5°-105° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 2.38 (s, CH3); 3.79 (s, 3H, OCH3); 4.07 (s, 2H, CH2CS); 7.23 (s, 4H, C6H4); 8.68 (bs, 1H, NH); 9.52 (bs, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. customevaporated in vacuo
  4. concentrationThe residue was concentrated at high vacuum and 45° C. for one hour
  5. customThe oily residue was chromatographed on a 75×800mm
  6. customdry column of silica gel
  7. washeluting with dichloromethane
  8. customthe solid crystallized from toluene-hexane

Sources & evidence

ORD record
ord-a220ffcaad094e4081285d5cbd102b99
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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