Water → HCID 22009651, compound

HRID 322447Notes

Reaction equation

HRID 322447 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)=[CH:17][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[C:33]1([CH:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[O:9][CH:10]=[C:11]([CH2:13][O:14][C:15]4[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][N:24]5[CH:28]=[CH:27][N:26]=[CH:25]5)=[CH:17][CH:16]=4)[N:12]=3)=[CH:6][CH:7]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7035ChlorodiphenylmethaneHCID 24758Sodium hydrideHCID 135819169HCID 135819169, compound

Product 1

HCID 22009651HCID 22009651, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-hydroxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (250 mg) in N,N-dimethylformamide (10 ml) was added sodium hydride (oily, 60%, 30 mg) and stirred at room temperature for one hour, to which chlorodiphenylmethane (270 mg) was added and stirred at 80° C. for 6 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N-sodium hydroxide and water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (50:1, v/v), crystals of 2-(4-diphenylmethoxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (155 mg, 43%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 106-107° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with 1N-sodium hydroxide and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-methanol (50:1

Sources & evidence

ORD record
ord-5d44d4026f164eeab89e3ff7f85072ad
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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