Epichlorohydrin → HCID 86729445, compound

HRID 1507026Notes

Reaction equation

HRID 1507026 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.Cl[CH2:21][CH:22]1[CH2:24][O:23]1>CN(C=O)C.O>[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:21][CH:22]4[CH2:24][O:23]4)[CH:14]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 59474456HCID 59474456, compound

Product 1

HCID 86729445HCID 86729445, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (161 mg, 6.69 mmol) in DMF (5 mL) was added 3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenol (500 mg, 2.23 mmol) at 27° C. After 0.5 h, 2-(chloromethyl)oxirane (246 mg, 2.68 mmol) was added and the reaction mixture was stirred 16 h, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was used in next step without further purification. (500 mg, yield 80%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was used in next step without further purification

Sources & evidence

ORD record
ord-29e68021713b4676a713aaa4515308a2
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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