Dimethylcarbamoyl Chloride → HCID 14819625, compound

HRID 1493580Notes

Reaction equation

HRID 1493580 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:13]=4[C:7]=3[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:28][N:29]([CH3:33])[C:30]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:13]=4[C:7]=3[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1)=[O:31].[CH3:28][N:29]([CH3:33])[C:30]([C:17]1[CH:18]=[CH:19][C:13]2[C:7]3[C:8](=[O:12])[NH:9][C:10]4[C:5]([C:6]=3[O:15][C:14]=2[CH:16]=1)=[CH:4][CH:3]=[C:2]([OH:1])[CH:11]=4)=[O:31]

Participants

7

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 10061491HCID 10061491, compound

Product 2

HCID 14819625HCID 14819625, compoundHCID 19830068HCID 19830068, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

In 1.0 ml of dry N,N-dimethylformamide was dissolved 100 mg of 3,9-dihydroxy-5H-benzofuro[3,2-c]quinolin-6-one. To the solution were added successively 7.8 μl of triethylamine, 40 mg of dimethylcarbamyl chloride and 3 mg of 4-dimethylaminopyridine, and the mixture was stirred for 15 hours at room temperature. The reaction mixture was evaporated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: chloroform/methanol/ethyl ether=10/1/2 by volume) to obtain 40 mg of 3-(N,N-dimethylcarbamoyloxy)-9-hydroxy-5H-benzofuro[3,2-c]quinolin-6-one and 25 mg of 9-(N,N-dimethylcarbamoyl)-3-hydroxy-5H-benzofuro[3,2-c]quinolin-6-one.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: chloroform/methanol/ethyl ether=10/1/2 by volume)

Sources & evidence

ORD record
ord-5dd76ea1921946519da995ea068acbcb
Source dataset
uspto-grants-1991_06
Patent number
US05023261

Reaction notes

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