Ammonia → HCID 178488159, compound

HRID 867879Notes

Reaction equation

HRID 867879 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]2[NH:18][C:19]([S:21][CH2:22][C:23]3[N:28]=[C:27]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:26]=[CH:25][N:24]=3)=[N:20][C:16]=2[CH:15]=1.N>ClCCl>[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]2[NH:18][C:19]([S:21]([CH2:22][C:23]3[N:28]=[C:27]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:26]=[CH:25][N:24]=3)=[O:9])=[N:20][C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acid2×HCID 178488127HCID 178488127, compound

Product 1

HCID 178488159HCID 178488159, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (1.69 g) in dichloromethane (25 ml) was added to a stirred solution of 5-methoxy-2-[4-piperidino-2-pyrimidinylmethylthio]-(1H)benzimidazole (3.48 g) in dichloromethane (75 ml) cooled to between -30° and -35°. After 1.5 hours at -20° a further quantity of m-chloroperbenzoic acid (0.34 g) was added. After a further 30 minutes ammonia was passed through the reaction mixture and the precipitated solid filtered off. The filtrate was washed with aqueous sodium carbonate, which was back washed with chloroform. The combined organic phases were dried (K2CO3) stripped and the residue purified by column chromatography (silica gel, 2% MeOH-NH3 /CHCl3) to give 5-methoxy-2-(4-piperidino-2-pyrimidinylmethylsulphinyl)-(1H)-benzimidazole (3.28 g) as an oil.

Workup

  1. temperaturecooled to between -30° and -35°
  2. filtrationthe precipitated solid filtered off
  3. washThe filtrate was washed with aqueous sodium carbonate, which
  4. washwas back washed with chloroform
  5. dry with materialThe combined organic phases were dried (K2CO3)
  6. customthe residue purified by column chromatography (silica gel, 2% MeOH-NH3 /CHCl3)

Sources & evidence

ORD record
ord-9fab4cfd7652439ea03bf9a4fcfae75d
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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