Ammonia → HCID 178430597, compound

HRID 1655220Notes

Reaction equation

HRID 1655220 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[N:12]1([C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([CH2:25][S:26][C:27]3[NH:31][C:30]4[CH:32]=[CH:33][C:34]([O:36][C:37]([F:42])([F:41])[CH:38]([F:40])[F:39])=[CH:35][C:29]=4[N:28]=3)[C:19]=2[Cl:43])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.N.C(#N)C>ClCCl>[N:12]1([C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([CH2:25][S:26]([C:27]3[NH:31][C:30]4[CH:32]=[CH:33][C:34]([O:36][C:37]([F:41])([F:42])[CH:38]([F:39])[F:40])=[CH:35][C:29]=4[N:28]=3)=[O:9])[C:19]=2[Cl:43])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 70297m-Chloroperbenzoic acidHCID 178430596HCID 178430596, compound

Product 1

HCID 178430597HCID 178430597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (0.75 g total) in dichloromethane (40 ml) was added to a solution of 2-(4-piperidino-3-chloro-5-methyl-2-pyridylmethylthio)-5-(1, 1,2,2-tetrafluoroethoxy)-(1H)-benzimidazole (1.5 g) in dichloromethane (30 ml) at -40° to -50° over a period of 2.5 hours. After a further 0.5 hour ammonia was passed through the solution and the precipitate filtered off and washed well with dichloromethane. The filtrates were evaporated under reduced pressure to give an oil which, on treatment with acetonitrile, gave 2-(4-piperidino-3-chloro-5-methyl-2-pyridylmethylsulphinyl)-5-(1, 1,2,2-tetrafluoroethoxy)-(1H)-benzimidazole, 0.77 g. m.p. 155°-56° (dec).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed well with dichloromethane
  3. customThe filtrates were evaporated under reduced pressure
  4. customto give an oil which

Sources & evidence

ORD record
ord-6318209597dd49d78933414f10a101a2
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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