Methyl carbazate → 4-(3,5-Dichlorophenyl)-1-(methoxycarbonyl)semicarbazide

HRID 1838458Notes

Reaction equation

HRID 1838458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:12]([C:14]([O:16][CH3:17])=[O:15])[NH2:13]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:11])[NH:13][NH:12][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 944603,5-Dichlorophenyl isocyanate

Product 1

HCID 172693274-(3,5-Dichlorophenyl)-1-(methoxycarbonyl)semicarbazideYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,5-Dichlorophenyl isocyanate (25 g, 133 mmol) was added dropwise to a cooled solution of methyl hydrazinocarboxylate (12 g, 133 mmol) in dry toluene (250 ml), with the temperature in the reaction flask maintained below 10° C. during the addition. After 28 h at RT, the precipitate was filtered, washed with toluene and isopropyl ether, and dried to yield the above compound as a white solid (30.3 g, mp=246° C.).

Workup

  1. temperaturemaintained below 10° C. during the addition
  2. filtrationthe precipitate was filtered
  3. washwashed with toluene and isopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-59b99eeed0184b588d4000224f318ed0
Source dataset
uspto-grants-2004_01
Patent number
US06673825B2

Reaction notes

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