m-Chloroperbenzoic acid → HCID 86738136, compound

HRID 1659320Notes

Reaction equation

HRID 1659320 reaction equation
[C:1]1([Se:7][C:8]2[CH:21]=[CH:20][C:11]3[N:12]=[C:13]([NH:15][C:16]([O:18][CH3:19])=[O:17])[NH:14][C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(O)(=O)C>[C:1]1([Se:7]([C:8]2[CH:21]=[CH:20][C:11]3[N:12]=[C:13]([NH:15][C:16]([O:18][CH3:19])=[O:17])[NH:14][C:10]=3[CH:9]=2)=[O:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20560297HCID 20560297, compound

Product 1

HCID 86738136HCID 86738136, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 5-phenylseleno-2-benzimidazolecarbamate (5.0 g, 14.5 mmole) in acetic acid (50 ml.) was cooled to 10°-15° C. while 85% 3-chloroperbenzoic acid (3.0 g, 14.7 mmole) was added in portions. The solution was then allowed to warm to room temperature, and the solvent was evaporated under reduced pressure. The residue was stirred with sodium carbonate solution and filtered, and the solid product was crystallised from a mixture of equal parts of acetic acid and methanol, to give methyl 5-phenylseleninyl-2-benzimidazolecarbamate, m.p. 222° C. with decomposition. All other 5-phenylseleninylbenzimidazole carbamates of the invention may be manufactured in exactly the same manner, by using the appropriate 1-6C alkyl 5-(optionally substituted phenyl)seleno-2-benzimidazolecarbamate in place of methyl 5-phenylseleno-2-benzimidazolecarbamate.

Workup

  1. additionwas added in portions
  2. customthe solvent was evaporated under reduced pressure
  3. filtrationfiltered
  4. customthe solid product was crystallised from a mixture of equal parts of acetic acid and methanol

Sources & evidence

ORD record
ord-40ec88fa63894394bd293388399223e3
Source dataset
uspto-grants-1981_12
Patent number
US04303666

Reaction notes

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