Sodium Hydroxide → HCID 178488129, compound

HRID 1655230Notes

Reaction equation

HRID 1655230 reaction equation
[OH-].[Na+].Cl.Cl[CH2:5][C:6]1[C:11]([F:12])=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:9]=[CH:8][N:7]=1.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]2[NH:25][C:26]([SH:28])=[N:27][C:23]=2[CH:22]=1>C(O)C>[O:16]1[CH2:17][CH2:18][N:13]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][S:28][C:26]3[NH:25][C:24]4[CH:29]=[CH:30][C:21]([O:20][CH3:19])=[CH:22][C:23]=4[N:27]=3)[C:11]=2[F:12])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 197911192-Chloromethyl-3-fluoro-4-morpholinopyridine hydrochlorideHCID 178488140HCID 178488140, compound

Product 1

HCID 178488129HCID 178488129, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5N NaOH (3.39 ml) was added dropwise to a stirred solution of 2-chloromethyl-3-fluoro-4-morpholinopyridine hydrochloride (2.06 g) and 5-methoxy-(1H)-benzimidazole-2-thiol (1.39 g) in ethanol (35 ml). After 3 hours excess solvent was removed and the residue treated with water (80 ml) and extracted with dichloromethane. The extracts were washed with water, dried (K2CO3), excess solvent removed and the residue crystallised from ethyl acetate to yield 2-(4-morpholino-3-fluoro-2-pyridylmethylthio)-5-methoxy-(1H)-benzimidazole (2.16 g) m.p. 121°-123°.

Workup

  1. customAfter 3 hours excess solvent was removed
  2. additionthe residue treated with water (80 ml)
  3. extractionextracted with dichloromethane
  4. washThe extracts were washed with water
  5. dry with materialdried (K2CO3), excess solvent
  6. customremoved
  7. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-b6b5e8f4a10a43efaa1a534c3602f7ba
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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