Dimethylcarbamoyl Chloride → HCID 13753208, compound

HRID 1732155Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2.5 g of 2-[p-(p-fluorophenoxy)phenoxy]-ethanol in 25 ml of dimethylformamide is added dropwise during 20 minutes while stirring to a suspension of 0.5 g of sodium hydride (55% in oil) in 5 ml of dimethylformamide. The mixture is then allowed to stir at 40° C. for 4 hours, then treated dropwise with 1.18 g of dimethylcarbamoyl chloride and allowed to react at 40° C. for 16 hours. The cooled mixture is poured into 75 ml of ice/water and extracted three times with 50 ml of ethyl acetate each time. The extracts are washed three times with 50 ml of water each time, dried and evaporated. The residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (85:15) to yield pure [2-[p-(p-fluorophenoxy)phenoxy]-ethyl]N,N-dimethylcarbamate; nD20 =1.5444.

Workup

customto react at 40° C. for 16 hours
extractionextracted three times with 50 ml of ethyl acetate each time
washThe extracts are washed three times with 50 ml of water each time
customdried
customevaporated
customThe residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (85:15)

Sources & evidence

ORD record: ord-c6163e5c6b234ee7b65d441e85bbb8d9
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04625048

Reaction notes

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