Diethylcarbamoyl chloride → HCID 21283644, compound

HRID 2232569Notes

Reaction equation

HRID 2232569 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]=[C:7]2[OH:20])([O-:3])=[O:2].[CH2:21]([N:23]([CH2:27][CH3:28])[C:24](Cl)=[O:25])[CH3:22].C(N(CC)CC)C>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:21]([N:23]([CH2:27][CH3:28])[C:24](=[O:25])[O:20][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)[CH3:22]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178526467HCID 178526467, compound

Product 1

HCID 21283644HCID 21283644, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The procedure is as in Example 70, starting with 6-nitro-2-phenyl-4-hydroxyquinoline (6 g) in tetrahydrofuran (60 cc), N,N-diethylcarbamoyl chloride (6.1 g), triethylamine (6.3 cc) and 4-dimethylaminopyridine (1.3 g). The residue is recrystallized twice in ethyl acetate. 6-Nitro-2-phenyl-4-quinolyl diethylcarbamate (6.4 g), m.p. 40° C., is thereby obtained.

Workup

  1. customThe residue is recrystallized twice in ethyl acetate

Sources & evidence

ORD record
ord-d5a39d5e98e14768829080054068e7bf
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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