Dimethylformamide → 1-[4-[2-(2,3-Dihydro-2,2-dimethyl-7-benzofuranyl) ethyloxy]phenyl]-3-methoxy-3-methylurea

HRID 1032609Notes

Reaction equation

HRID 1032609 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[CH3:22][C:23]1([CH3:35])[CH2:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:31]([CH2:32][CH2:33]Cl)[C:25]=2[O:24]1>O>[CH3:22][C:23]1([CH3:35])[CH2:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:31]([CH2:32][CH2:33][O:1][C:2]3[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[CH:4][CH:3]=3)[C:25]=2[O:24]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13254818N'-(4-Hydroxyphenyl)-N-methoxy-N-methylureaHCID 149982742-(2,3-Dihydro-2,2-dimethyl-7-benzofuranyl)ethyl chloride

Product 1

HCID 144998741-[4-[2-(2,3-Dihydro-2,2-dimethyl-7-benzofuranyl) ethyloxy]phenyl]-3-methoxy-3-methylureaYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g of 1-(4-hydroxyphenyl)-3-methoxy-3-methylurea was dissolved into 20 ml of dried N,N-dimethylformamide, and 0.6 g of 60% sodium hydride was added thereto. After the mixture was stirred for 30 minutes, 1.7 g of 2-(2,3-dihydro-2,2-dimethyl-7-benzofuranyl)ethyl chloride was added dropwise thereto under cooling with ice. After the mixture was stirred at room temperature for 5 hours, it was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 2.0 g of Compound No. 10 shown in Table 1.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringAfter the mixture was stirred at room temperature for 5 hours
  4. extractionextracted with ethyl acetate
  5. washAfter the organic layer was washed with water, it
  6. dry with materialwas dried over anhydrous magnesium sulfate and ethyl acetate
  7. distillationwas distilled off

Sources & evidence

ORD record
ord-d9e5289aa78a4c71a4e06a368375033c
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

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