Sulfuryl chloride → Ethyl 6-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

HRID 1643920Notes

Reaction equation

HRID 1643920 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[NH:3]1.S(Cl)([Cl:19])(=O)=O>C(O)(=O)C>[Cl:19][C:13]1[CH:14]=[CH:15][C:4]2[NH:3][C:2](=[O:1])[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylate

Product 1

HCID 10354291Ethyl 6-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7.00 g (33.9 mmol) of ethyl 2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (IV) and 3.02 ml (37.3 mmol) of sulfuryl chloride in acetic acid (90 ml) was stirred at 90° C. for 1 h. The cooled reaction mixture was poured into ice-water. The precipitated solid was filtered off, washed with water, dried in vacuo and recrystallized from ethyl acetate.

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. customdried in vacuo
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ab703d4154b44b05a2319041a0d3e6c1
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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