Methyl carbazate → HCID 14294138, compound

HRID 1381697Notes

Reaction equation

HRID 1381697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](C(S)C(OCC)=O)=[S:11])=[CH:5][CH:4]=1.[NH:19]([C:21]([O:23][CH3:24])=[O:22])[NH2:20]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([NH:20][NH:19][C:21]([O:23][CH3:24])=[O:22])=[S:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 21682419HCID 21682419, compound

Product 1

HCID 14294138HCID 14294138, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 50 g of the above ester, 18.2 g of methyl hydrazinocarboxylate and 300 ml of dichloromethane was refluxed for 2 hours, then washed twice with water, once with saturated sodium chloride and dried. The resulting oily residue was concentrated under high vacuum at 50° C. for 2 hours and the semi-solid crystallized from toluene-hexane, giving 36 g of the desired compound as ivory colored crystals, mp 94.5°-95° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 3.78 (s, 3H, OCH3); 3.80 (s, 3H, OCH3); 4.03 (s, 2H, CH2CS); [6.89 (d, 2H, J=8.2 Hz) and 7.21 (d, 2H)(C6H4)]8.60 (bs, 1H, NH); 9.40 (bs, 1H, NH).

Workup

  1. temperaturewas refluxed for 2 hours
  2. washwashed twice with water, once with saturated sodium chloride
  3. customdried
  4. concentrationThe resulting oily residue was concentrated under high vacuum at 50° C. for 2 hours
  5. customthe semi-solid crystallized from toluene-hexane

Sources & evidence

ORD record
ord-8561d13e828443e1b7d592e5e2cbe8cc
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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