Ammonia → HCID 178488164, compound

HRID 1655237Notes

Reaction equation

HRID 1655237 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:38]=[CH:37][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][O:33][CH2:32][CH2:31]4)[C:26]([F:36])=[CH:25][N:24]=3)=[N:20][C:16]=2[CH:15]=1.N>ClCCl>[O:33]1[CH2:32][CH2:31][N:30]([C:27]2[C:26]([F:36])=[CH:25][N:24]=[C:23]([CH2:22][S:21]([C:19]3[NH:18][C:17]4[CH:37]=[CH:38][C:14]([O:13][CH3:12])=[CH:15][C:16]=4[N:20]=3)=[O:9])[C:28]=2[CH3:29])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acid3×HCID 178488134HCID 178488134, compound

Product 1

HCID 178488164HCID 178488164, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

m-Chloroperbenzoic acid (0.48 g) in dichloromethane (10 ml) was added dropwise to a stirred solution of 5-methoxy-2-(4-morpholino-5-fluoro-3-methyl-2-pyridylmethylthio)-(1H)-benzimidazole (1.1 g) in dichloromethane (50 ml) at -30° to -35°. After 0.5 hour at -30° a further addition of m-chloroperbenzoic acid (0.048 g) in dichloromethane (2 ml) was made and the mixture stirred for a further 0.5 hour. After a further addition of m-chloroperbenzoic acid (0.048 g) in dichloromethane (2 ml) and after standing for a further 0.5 hour at -30°, ammonia gas was passed through the solution and the precipitated benzoate salts filtered off. The filtrate was evaporated to dryness and the residue crystallised from ethyl acetate to yield 2-(4-morpholino-5-fluoro-3-methyl -2-pyridylmethylsulphinyl)-5-methoxy-(1H)-benzimidazole (0.8 g) m.p. 158°-160°.

Workup

  1. waitafter standing for a further 0.5 hour at -30°
  2. filtrationthe precipitated benzoate salts filtered off
  3. customThe filtrate was evaporated to dryness
  4. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-f90a0cdda3ee4079b736b486bb19570e
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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