1,2,3,4-Tetrahydro-1-naphthylamine → 1-Benzoyl-3-(1,2,3,4-tetrahydro-1-naphthyl)urea

HRID 2072368Notes

Reaction equation

HRID 2072368 reaction equation
[CH:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[C:12]([NH:20][C:21]([NH:11][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 78210Benzoyl isocyanate

Product 1

HCID 205373051-Benzoyl-3-(1,2,3,4-tetrahydro-1-naphthyl)ureaYield 78.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 1,2,3,4-tetrahydro-1-naphthylamine (10.01 g) and ether (100 ml) is stirred under a nitrogen atmosphere and a solution of benzoyl isocyanate (9.99 g) in ether (90 ml) is added dropwise. After the addition is completed, the mixture is stirred for 0.5 hour and cooled in ice. The product is collected and washed with cold ether (50 ml) to afford 15.7 g of the title compound, m.p. 166° to 169° C. Recrystallization from acetone affords 13.61 g, m.p. 171° to 173° C.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred for 0.5 hour
  3. temperaturecooled in ice
  4. customThe product is collected
  5. washwashed with cold ether (50 ml)

Sources & evidence

ORD record
ord-9056e843da3b40b6b9fc88851b80746c
Source dataset
uspto-grants-1977_09
Patent number
US04051183

Reaction notes

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