Ammonia → HCID 178488161, compound

HRID 1655231Notes

Reaction equation

HRID 1655231 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]([F:29])=[C:27]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:26]=[CH:25][N:24]=3)=[N:20][C:16]=2[CH:15]=1.N>ClCCl>[O:33]1[CH2:34][CH2:35][N:30]([C:27]2[CH:26]=[CH:25][N:24]=[C:23]([CH2:22][S:21]([C:19]3[NH:18][C:17]4[CH:36]=[CH:37][C:14]([O:13][CH3:12])=[CH:15][C:16]=4[N:20]=3)=[O:9])[C:28]=2[F:29])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acid2×HCID 178488129HCID 178488129, compound

Product 1

HCID 178488161HCID 178488161, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

m-Chloroperbenzoic acid (1.06 g) in dichloromethane (50 ml) was added dropwise to a stirred solution of 5-methoxy-2-(4-morpholino-3-fluoro-2-pyridylmethylthio)-(1H)-benzimidazole (2.31 g) in dichloromethane (50 ml) at -30° to -35°. After 0.5 hour at -30° a further addition of m-chloroperbenzoic acid (0.106 g) in dichloromethane (15 ml) was made and the mixture stirred for a further 20 minutes at -30°. Ammonia gas was then 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-3-fluoro-2-pyridylmethylsulphinyl)-5-methoxy-(1H)-benzimidazole (1.75 g) m.p. 142°-46°

Workup

  1. filtrationthe precipitated benzoate salts filtered off
  2. customThe filtrate was evaporated to dryness
  3. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-3d88d4d074284bc2b97082fff8054079
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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