m-Chloroperbenzoic acid → HCID 178502045, compound

HRID 838998Notes

Reaction equation

HRID 838998 reaction equation
[Cl:1][C:2]1([Cl:22])[CH2:4][C:3]1([CH2:6][S:7][C:8]1[CH:21]=[CH:20][C:11]2[NH:12][C:13]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[N:14][C:10]=2[CH:9]=1)[CH3:5].ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:22][C:2]1([Cl:1])[CH2:4][C:3]1([CH2:6][S:7]([C:8]1[CH:21]=[CH:20][C:11]2[NH:12][C:13]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[N:14][C:10]=2[CH:9]=1)=[O:28])[CH3:5]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178502041HCID 178502041, compound

Product 1

HCID 178502045HCID 178502045, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 7.2 g (0.2 mole) of [5-[[(2,2-dichloro-1-methylcyclopropyl)methyl]thio]-1H-benzimidazol-2-yl]carbamic acid, methyl ester in 120 ml of CHCl3 and 120 ml of acetic acid at -15° C there is added 4.2 g (0.02 mole) of 85% m-chloroperoxybenzoic acid and 40 ml of CHCl3 and with stirring is allowed to warm to room temperature. The mixture is stirred for an additional 2 hours. The CHCl3 is removed in vacuo and the remaining solution is neutralized with aqueous NaHCO3. The resulting solid is filtered off, dried, and crystallized from acetonitrile to yield 3.4 g of the title compound, m.p. 231-233° C.

Workup

  1. stirringThe mixture is stirred for an additional 2 hours
  2. customThe CHCl3 is removed in vacuo
  3. filtrationThe resulting solid is filtered off
  4. customdried
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-49242e090d5e4684a2d86d6bf39d467e
Source dataset
uspto-grants-1978_06
Patent number
US04093732

Reaction notes

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