Dimethylcarbamoyl Chloride → HCID 13505950, compound

HRID 1981527Notes

Reaction equation

HRID 1981527 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:13][N:14]([CH3:18])[C:15](=[O:16])[NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13505950HCID 13505950, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

6-Amino-3,4-dihydrocarbostyril (1 g) is suspended in benzene (20 ml), and thereto is added dropwise a solution of N,N-dimethylcarbamoyl chloride (0.86 ml) in benzene (10 ml) at room temperature. The mixture is reacted at 50° C. for 3 hours, and thereto is added triethylamine (0.86 ml), and the mixture is further reacted at 50° to 60° C. for 5 hours. After the reaction, benzene is distilled off under reduced pressure, and water is added to the residue. The resulting precipitate is separated by filtration and washed with water. The crystal thus obtained is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1) and then recrystallized from methanol-diethyl ether to give 6-(3,3-dimethylureido)-3,4-dihydrocarbostyril (0.6 g), as colorless prisms, m.p. 181°-183° C.

Workup

  1. customThe mixture is reacted at 50° C. for 3 hours
  2. customthe mixture is further reacted at 50° to 60° C. for 5 hours
  3. distillationis distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. customThe resulting precipitate is separated by filtration
  6. washwashed with water
  7. customThe crystal thus obtained
  8. customis purified by silica gel column chromatography (solvent; chloroform:methanol=100:1)
  9. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-3b02c045567241c2a030a9e59ce9f1b1
Source dataset
uspto-grants-1986_06
Patent number
US04593035

Reaction notes

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