Methyl carbazate → HCID 14294123, compound

HRID 1381701Notes

Reaction equation

HRID 1381701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](C(S)C(OCC)=O)=[S:10])=[CH:4][CH:3]=1.[NH:18]([C:20]([O:22][CH3:23])=[O:21])[NH2:19]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:19][NH:18][C:20]([O:22][CH3:23])=[O:21])=[S:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 86742730HCID 86742730, compound

Product 1

HCID 14294123HCID 14294123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 130 g of 2-[2-(4-chlorophenyl)-1-thioxoethyl]thioglycolic acid, ethyl ester, 45 g of methyl hydrazinocarboxylate and 500 ml of dichloromethane was heated at reflux for 4 hours, then concentrated in vacuo. The residue was taken up in 1.2 liters of ether and extracted with three 500 ml portions of 0.5N sodium hydroxide. The alkaline extracts were combined, washed with ether and acidified with 6N hydrochloric acid to pH 4. The solution was extracted three times with a mixture of ether and dichloromethane. The organic phases were combined and concentrated. The residual oil was concentrated at 70°-75° C. for one hour at 0.1 mmHg. The residue was crystallized from acetone-methylcyclohexane and then from toluene, giving the desired product as ivory colored crystals, mp 147.5°-148° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 3.80 (s, 3H, OCH3); 4.03 (s, 2H, CH2CS); 7.31 (bs, 4H, C6H4); 8.60 (bs, 1H, NH); 9.90 (bs, 1H, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. concentrationconcentrated in vacuo
  4. extractionextracted with three 500 ml portions of 0.5N sodium hydroxide
  5. washwashed with ether
  6. extractionThe solution was extracted three times
  7. additionwith a mixture of ether and dichloromethane
  8. concentrationconcentrated
  9. concentrationThe residual oil was concentrated at 70°-75° C. for one hour at 0.1 mmHg
  10. customThe residue was crystallized from acetone-methylcyclohexane

Sources & evidence

ORD record
ord-2297fbc7193d48808e9079c629d3ff0e
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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