O-Methylhydroxylamine → 1-Methoxy-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)urea

HRID 1730726Notes

Reaction equation

HRID 1730726 reaction equation
[CH3:1][O:2][NH2:3].C(N(CC)CC)C.[O:11]=[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]([N:22]=[C:23]=[O:24])[CH2:14][CH2:13]1>C(Cl)Cl>[CH3:1][O:2][NH:3][C:23]([NH:22][CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:11])[CH2:13][CH2:14]1)=[O:24]

Participants

5

Reactant 3

HCID 4113O-MethylhydroxylamineHCID 8471TriethylamineHCID 203516844-Isocyanato-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 203516951-Methoxy-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-methoxyamine (2.5 g), triethylamine (3.04 g) and dry methylene chloride (50 ml) is stirred at room temperature for 20 minutes under a nitrogen atmosphere. Then a solution of 1,2,3,4-tetrahydro-4-oxo-1-naphthyl isocyanate (5.62 g) in dry methylene chloride (50 ml) is added dropwise. After stirring at room temperature for 40 minutes, the reaction mixture is evaporated to dryness in vacuo and the solid residue washed with water (3 × 150 ml) to yield 6.1 g. title product, m.p. 148° to 151° C. Recrystallization from benzene affords crystals, m.p. 155° to 158° C.

Workup

  1. stirringAfter stirring at room temperature for 40 minutes
  2. customthe reaction mixture is evaporated to dryness in vacuo
  3. washthe solid residue washed with water (3 × 150 ml)
  4. customto yield 6.1 g

Sources & evidence

ORD record
ord-c897f0c38b0f4aecaa7953b7178bd282
Source dataset
uspto-grants-1976_11
Patent number
US03993677

Reaction notes

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