2-Chlorobenzoyl isocyanate → 3-(4-[4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy]-3,5-dimethylphenyl)-1-(2-chlorobenzoyl) urea

HRID 2295794Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][C:13]2[C:19]([CH3:20])=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[CH3:21])=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=1[C:25]([N:27]=[C:28]=[O:29])=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][C:13]2[C:14]([CH3:21])=[CH:15][C:16]([NH:17][C:28](=[O:29])[NH:27][C:25](=[O:26])[C:24]3[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=3[Cl:22])=[CH:18][C:19]=2[CH3:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution containing 3.0 g of 4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethylaniline in 40 mL of toluene under an atmosphere of nitrogen and heated to 70° C. (internal) was slowly added a solution containing 2.7 g of 2-chlorobenzoyl isocyanate in 5 mL of toluene. The resulting mixture was heated at 70° C. for 1/2 hour. The reaction mixture was cooled to 0° C. and filtered. The collected solid was washed with toluene and then hexane. It was dried under vacuum to afford 3.58 g of a white solid, mp. 224°-226° C. NMR (DMSO-d6): 1.7-2.2 (m, 10H, contains singlet at 2.03), 2.7-3.0 (m, 4H), 6.07 (d, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 1H), 7.4-7.7 (m, 4H), 10.38 (S, 1H), 11.20 (S, 1H).

Workup

additionwas slowly added a solution
temperatureThe resulting mixture was heated at 70° C. for 1/2 hour
temperatureThe reaction mixture was cooled to 0° C.
filtrationfiltered
washThe collected solid was washed with toluene
customIt was dried under vacuum

Sources & evidence

ORD record: ord-87cff853d0044341a1804b5d83aea849
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04426385

Reaction notes

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