Carbendazim → 2-(Methoxycarbonylamino)-benzimidazole-1-carboximidic acid phenyl ester

HRID 1076192Notes

Reaction equation

HRID 1076192 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)=[O:4].[C:15]1([O:21][C:22]#[N:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[C:15]1([O:21][C:22]([N:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=[C:6]2[NH:5][C:3]([O:2][CH3:1])=[O:4])=[NH:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 25429CarbendazimHCID 70740Phenyl cyanate

Product 1

HCID 543466602-(Methoxycarbonylamino)-benzimidazole-1-carboximidic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 420.6 g (2.2 mole) 2-(methoxycarbonylamino)-benzimidazole in 10 ltr chloroform a solution of 274 g (2.3 moles) phenyl cyanate in 2 ltr chloroform is added in drops while stirring at 20°C. The reaction mixture is stirred for 6 hours at room temperature and then left standing overnight. The product is then filtered and the solvent removed under vacuum. The colorless, crystalline residue is treated with ether.

Workup

  1. additionis added in drops
  2. stirringThe reaction mixture is stirred for 6 hours at room temperature
  3. waitleft
  4. filtrationThe product is then filtered
  5. customthe solvent removed under vacuum
  6. additionThe colorless, crystalline residue is treated with ether

Sources & evidence

ORD record
ord-d55c3db79b29404595ec8636659575bb
Source dataset
uspto-grants-1976_05
Patent number
US03956307

Reaction notes

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