Diethylcarbamoyl chloride → HCID 13769187, compound

HRID 2232524Notes

Reaction equation

HRID 2232524 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([OH:18])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:26]([N:28]([CH2:32][CH3:33])[C:29](Cl)=[O:30])[CH3:27]>CN(C)C=O>[CH2:26]([N:28]([CH2:32][CH3:33])[C:29](=[O:30])[O:18][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[N:9]=1)[CH3:27]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178423641HCID 178423641, compound

Product 1

HCID 13769187HCID 13769187, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 37, starting with 3-(4-methylphenyl)-1-isoquinolinol (4.7 g), triethylamine (8.1 g) and diethylcarbamoyl chloride (10.8 g) in dimethylformamide (50 cc). After chromatography on silica gel with a cyclohexane/ethyl acetate (4:1 by volume) mixture as eluant and recrystallization in ethyl ether, 3-(4-methylphenyl)-1-isoquinolyl diethylcarbamate (0.6 g), m.p. 98° C., is obtained.

Workup

  1. customAfter chromatography on silica gel with a cyclohexane/ethyl acetate (4:1 by volume) mixture as eluant and recrystallization in ethyl ether

Sources & evidence

ORD record
ord-3035aa92915944a5a7f8fff66b97d114
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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