Ammonia → HCID 178488165, compound

HRID 620169Notes

Reaction equation

HRID 620169 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:37]=[CH:36][C:17]2[NH:18][C:19]([S:21][CH2:22][C:23]3[C:28]([CH3:29])=[C:27]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[N:26]=[CH:25][N:24]=3)=[N:20][C:16]=2[CH:15]=1.N>ClCCl>[CH3:12][O:13][C:14]1[CH:37]=[CH:36][C:17]2[NH:18][C:19]([S:21]([CH2:22][C:23]3[C:28]([CH3:29])=[C:27]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[N:26]=[CH:25][N:24]=3)=[O:9])=[N:20][C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acidHCID 178488135HCID 178488135, compound

Product 1

HCID 178488165HCID 178488165, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (2.16 g) in dichloromethane (40 ml) was added to a stirred solution of 5-methoxy-2-(5-methyl-6-piperidino-4-pyrimidinylmethylthio)-(1H)-benzimidazole (4.0 g) in dichloromethane (110 ml) cooled to between -40° and -50°. After a further hour at -40°, ammonia was passed through the reaction mixture and the precipitated solid filtered off. The filtrate was stripped, and the residual glass triturated with acetonitrile to give 5-methoxy-2-(5-methyl-6-piperidino-4-pyrimidinylmethylsulphinyl)-(1H)-benzimidazole 2.66 g, m.p. 87°-89°.

Workup

  1. temperaturecooled to between -40° and -50°
  2. waitAfter a further hour at -40°
  3. filtrationthe precipitated solid filtered off
  4. customthe residual glass triturated with acetonitrile

Sources & evidence

ORD record
ord-c295573e3d6d41ddad39e96c09d5a0f6
Source dataset
uspto-grants-1989_04
Patent number
US04820708

Reaction notes

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