Sodium Hydroxide → HCID 178430596, compound

HRID 1655219Notes

Reaction equation

HRID 1655219 reaction equation
[OH-].[Na+].Cl.[N:4]1([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17]Cl)[C:11]=2[Cl:19])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[F:20][C:21]([F:36])([O:25][C:26]1[CH:35]=[CH:34][C:29]2[N:30]=[C:31]([SH:33])[NH:32][C:28]=2[CH:27]=1)[CH:22]([F:24])[F:23]>C(O)C>[N:4]1([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][S:33][C:31]3[NH:30][C:29]4[CH:34]=[CH:35][C:26]([O:25][C:21]([F:36])([F:20])[CH:22]([F:24])[F:23])=[CH:27][C:28]=4[N:32]=3)[C:11]=2[Cl:19])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 19791117HCID 19791117, compoundHCID 178506048HCID 178506048, compound

Product 1

HCID 178430596HCID 178430596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N Sodium hydroxide (2 ml) was added to a stirred suspension of 4-piperidino-3-chloro-5-methyl-2-chloromethylpyridine hydrochloride (1.6 g) and 5-(1,1,2,2-tetrafluoroethoxy)-2-mercaptobenzimidazole (1.5 g) in ethanol at room temperature. After standing over night an additional quantity of sodium hydroxide (1 ml) was added and after a further 1 hour the mixture was evaporated at reduced pressure. The residue was chromatographed (silica gel chloroform/methanol 2%) and crystallised from acetonitrile to give 2-(4-piperidino-3-chloro-5-methyl-2-pyridylmethylthio)-5-(1, 1,2,2-tetrafluoroethoxy)-(1H)-benzimidazole, 1.66 g, m.p. 170°-71°.

Workup

  1. waitAfter standing over night
  2. customwas evaporated at reduced pressure
  3. customThe residue was chromatographed (silica gel chloroform/methanol 2%)
  4. customcrystallised from acetonitrile

Sources & evidence

ORD record
ord-8eb3eee6d82a46859a54cf20a0675385
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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