Dimethylformamide → HCID 86729452, compound

HRID 1507043Notes

Reaction equation

HRID 1507043 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:14]=[C:15](O)[CH:16]=[CH:17][CH:18]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.Cl[CH2:21][C@@H:22]1[CH2:24][O:23]1.C[N:26](C=O)C>O>[CH3:3][N:4]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=3)[NH:26][CH2:21][C@H:22]3[CH2:24][O:23]3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 149428(+)-EpichlorohydrinHCID 59474456HCID 59474456, compound

Product 1

HCID 86729452HCID 86729452, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, (S)-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. (480 mg, yield 77%).

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-393322522af043ca87af2134947260ee
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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