Water → N-Methyl-N'-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)urea

HRID 372274Notes

Reaction equation

HRID 372274 reaction equation
Cl.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([NH2:13])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:21][N:22]=[C:23]=[O:24].O>O1CCCC1>[CH3:21][NH:22][C:23]([NH:13][CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:2])[CH2:4][CH2:5]1)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 203273204-Amino-1,2,3,4-tetrahydronaphthalen-1-one hydrochloride

Product 1

HCID 20327317N-Methyl-N'-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 10 g of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride in 200 ml of dry tetrahydrofuran (THF) under a nitrogen atmosphere, 76 ml of triethylamine is added dropwise. The mixture is stirred for an additional 5 minutes, and 3 ml of methylisocyanate is added dropwise. The reaction mixture is stirred for 1 hour at room temperature and the solid collected. The filter cake is washed with THF and then with 3 × 50 ml of water. The THF filtrate is concentrated in vacuo to afford some product. The water-insoluble solid is air dried to afford 8.8 g of the title compound melting point 219°-221° C. Recrystallization from about 150 ml of methanol yeilds 7.4 g of the above product, melting point 220°-223° C.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at room temperature
  2. customthe solid collected
  3. washThe filter cake is washed with THF
  4. concentrationThe THF filtrate is concentrated in vacuo
  5. customto afford some product
  6. customdried

Sources & evidence

ORD record
ord-f1990120165a47a684e236befdb5b50f
Source dataset
uspto-grants-1978_05
Patent number
US04089976

Reaction notes

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