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

HRID 616057Notes

Reaction equation

HRID 616057 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-6e0828acdbf749dab50c2766b1f4b020
Source dataset
uspto-grants-1978_02
Patent number
US04072711

Reaction notes

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