Reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[N:24]=[C:25]=[O:26])([CH3:14])[CH3:13].N1C=CC=CC=1>ClCCl>[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25]([NH:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]1)=[O:26])([CH3:13])[CH3:14]Participants
5
Procedure
To a solution of 1.6 g of 4-tert-butylcyclohexylamine in 15 ml of dichloromethane was added a solution of 2.2 g of 2,6-diisopropylphenylisocyanate in dichloromethane dropwise in the presence of pyridine at 0° C. Thereafter the mixture was stirred for 1.5 hours at room temperature and concentrated. The residue was partitioned between isopropyl ether and water, and the organic layer was successively washed with 0.5N hydrochloric acid, water and sodium sulfate solution. The organic layer was dried over magnesium sulfate and then distilled away. The resulting residue was crystallized from ethyl acetate to give 2.2 g of N-(2,6-diisopropylphenyl)-N'-(4-tert-butylcyclohexyl)urea, melting at 270° C.
Workup
- concentrationconcentrated
- customThe residue was partitioned between isopropyl ether and water
- washthe organic layer was successively washed with 0.5N hydrochloric acid, water and sodium sulfate solution
- dry with materialThe organic layer was dried over magnesium sulfate
- distillationdistilled away
- customThe resulting residue was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-6a6b231c3e824992b74412a4122da314
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420164
Linked notes
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