Methanol → Urea, 1-(2-chloroethyl)-3-(2-naphthyl)-

HRID 80103

Reaction equation

HRID 80103 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH2:17].CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 70572-NaphthylamineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 256650Urea, 1-(2-chloroethyl)-3-(2-naphthyl)-Yield 83.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-Chloro-2-isocyanato-ethane (0.81 mL, 9.42 mmol) was added dropwise to a stirred solution of naphthalen-2-ylamine (900 mg, 6.28 mmol) in toluene (50 mL) over a period of 30 minutes at 0° C. The reaction temperature was maintained at room temperature for 5 hours. The reaction was monitored by TLC (5% MeOH in chloroform). The reaction mixture was filtered, washed with toluene and dried under reduced pressure to afford 1.3 g (83% yield) of 1-(2-chloro-ethyl)-3-naphthalen-2-yl-urea.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-7d1e7ba22c45424894f9727198bc3033
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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