Toluene → HCID 15020189, compound

HRID 973447Notes

Reaction equation

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

Participants

Reactant 3

HCID 1140Toluene

HCID 853464-Octylaniline

HCID 6045371,3-Dichloro-2-isocyanatobenzene

Product 1

HCID 15020189HCID 15020189, compoundYield 68%

Procedure

To 10.6 ml (5.3 mmol) of a toluene solution of 0.50M 2,6-dichlorophenyl isocyanate was added 1.21 ml (5.32 mmol) of 4-octylaniline at room temperature and the whole was stirred for 16 hours. After removal of the solvent under reduced pressure, the residue was recrystallized from methanol to give 1.42 g (68% yield) of 1-(4-octylphenyl)-3-(2,6-dichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 1, No. 13, No. 14, No. 17, and No. 18 listed in Table 3 were similarly prepared as above.

Workup

customAfter removal of the solvent under reduced pressure
customthe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-f36d7a634bbd44d883a6b5f2c82c5312
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05063247

Reaction notes

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