Dimethylcarbamoyl Chloride → 1,1-Dimethyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)urea

HRID 441566Notes

Reaction equation

HRID 441566 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]([NH2:19])[CH2:11][CH2:10]1.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>ClCCl>[CH3:20][N:21]([CH3:25])[C:22]([NH:19][CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[O:8])[CH2:10][CH2:11]1)=[O:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 137386604-amino-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 203516891,1-Dimethyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 25 ml of dichloromethane containing 2.8 ml of triethyl amine, 2,32 g of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine are added followed by 2.16 g of dimethylcarbamoyl chloride. The mixture is heated at reflux for 3 hours, cooled to room temperature, washed successively with 50 ml of H2O, 50 ml of 3N NaOH, 50 ml of 3N HCl and 50 ml of H2O. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is recrystallized from toluene to give the title compound, melting point 157° C. to 162° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. washwashed successively with 50 ml of H2O, 50 ml of 3N NaOH, 50 ml of 3N HCl and 50 ml of H2O
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-70d4a303a22945b98a483405fd04cdf4
Source dataset
uspto-grants-1977_08
Patent number
US04041070

Reaction notes

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