m-Chloroperbenzoic acid → HCID 178502047, compound

HRID 616921Notes

Reaction equation

HRID 616921 reaction equation
[CH:1]1([CH2:7][S:8][C:9]2[CH:22]=[CH:21][C:12]3[NH:13][C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])=[N:15][C:11]=3[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl.CC(O)=O>[CH:1]1([CH2:7][S:8]([C:9]2[CH:22]=[CH:21][C:12]3[NH:13][C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])=[N:15][C:11]=3[CH:10]=2)=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178502042HCID 178502042, compound

Product 1

HCID 178502047HCID 178502047, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 3.2 g of [5-[(cyclohexylmethyl)thio]-1H-benzimidazol-2-yl]carbamic acid, methyl ester in 120 ml CHCl3 and 120 ml HOAc at -20° C there is added a solution of 2.1 g of m-chloroperbenzoic acid. The resulting mixture is stirred and allowed to warm to room temperature. Stirring is continued for 5 hours and then CHCl3 is removed in vacuo. Water is added and the solution is neutralized with NaHCO3. The resulting solid is filtered off and crystallized from acetonitrile (1.5 g) to give the title compound, m.p. 272°-274° C.

Workup

  1. stirringStirring
  2. customCHCl3 is removed in vacuo
  3. additionWater is added
  4. filtrationThe resulting solid is filtered off
  5. customcrystallized from acetonitrile (1.5 g)

Sources & evidence

ORD record
ord-6a597646a3334cbd8837cfc48acaa03a
Source dataset
uspto-grants-1978_02
Patent number
US04076828

Reaction notes

Loading…