Ammonia → HCID 178488160, compound

HRID 1655211Notes

Reaction equation

HRID 1655211 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25][C:26]3[NH:30][C:29]4[CH:31]=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:28]=4[N:27]=3)[C:19]=2[Cl:37])[CH2:14][CH2:13]1.N>ClCCl>[O:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25]([C:26]3[NH:30][C:29]4[CH:31]=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:28]=4[N:27]=3)=[O:9])[C:19]=2[Cl:37])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 70297m-Chloroperbenzoic acidHCID 178488128HCID 178488128, compound

Product 1

HCID 178488160HCID 178488160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (1.61 g) in dichloromethane (75 ml) was added dropwise to a stirred solution of 2 -(4 -morpholino-3 -chloro-2 -pyridylmethylthio)-5 -methoxy- (1H)-benzimidazole (3.35 g) in dichloromethane (150 ml) cooled to -35°. After 1 hour, ammonia was passed through the solution for 5 minutes and the precipitate filtered off. The solution was evaporated under reduced pressure and the residue chromatographed (silica gel, 2 % CHCl3 /MEOH-NH3 ) to give an oil which was crystallised from ethanol to give 2 -(4 -morpholino-3 -chloro-2 -pyridylmethylsulphinyl)-5 -methoxy-(1H)-benzimidazole. (2.6 g).

Workup

  1. temperaturecooled to -35°
  2. filtrationthe precipitate filtered off
  3. customThe solution was evaporated under reduced pressure
  4. customthe residue chromatographed (silica gel, 2 % CHCl3 /MEOH-NH3 )
  5. customto give an oil which
  6. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-c3a03ca742c34eabb33c26f1f6f6116a
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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