Dimethylformamide → 1-[4-(2,3-Dihydro-2,2-dimethyl-7-benzofuranylmethyloxy)phenyl]-3,3-dimethylurea

HRID 1032608Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11]Cl)[C:4]=2[O:3]1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:17][CH:16]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][O:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:19][CH:20]=3)[C:4]=2[O:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

3.0 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyl chloride and 3.0 g of 1-(4-hydroxyphenyl)-3,3-dimethylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture 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 4.0 g of Compound No. 7 shown in Table 1.

Workup

additionwas added
extractionextracted with ethyl acetate
washAfter the organic layer was washed with water, it
dry with materialwas dried over anhydrous magnesium sulfate and ethyl acetate
distillationwas distilled off

Sources & evidence

ORD record: ord-7e4396c81b394f1b8e8329ab0af6ea13
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04959092

Reaction notes

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