alpha-Naphthyl isocyanate → HCID 9840976, compound

HRID 2110083Notes

Reaction equation

HRID 2110083 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:14]1([N:24]=[C:25]=[O:26])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:13][O:12][C:11]1[C:2]([NH:1][C:25]([NH:24][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:26])=[CH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 2351413-Methoxynaphthalen-2-amine

Product 1

HCID 9840976HCID 9840976, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-3-methoxynaphthalene (0.253 g, 1.50 mmol) in CH2Cl2 (3 mL) at room temp. was added a solution of 1-naphthyl isocyanate (0.247 g, 1.50 mmol) in CH2Cl2 (2 mL) and the resulting mixture was allowed to stir overnight. The resulting precipitate was separated and washed with CH2Cl2 to give the desired urea as a white powder (0.450 g, 90%): mp 235-236° C.; 1H-NMR (DMSO-d6) δ 4.04 (s, 3H), 7.28-7.32 (m, 2H), 7.38 (s, 1H), 7.44-7.72 (m, 6H), 7.90-7.93 (m, 1H), 8.05-8.08 (m, 1H), 8.21-8.24 (m, 1H), 8.64 (s, 1H), 9.03 (s, 1H), 9.44 (s, 1H); FAB-MS m/z 343 ((M+H)+). B1f. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Workup

  1. customThe resulting precipitate was separated
  2. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-3a82f2efaa4042e68cbafd3fe773dc62
Source dataset
uspto-grants-2009_04
Patent number
US07517880B2

Reaction notes

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