2,6-Diisopropylphenyl isocyanate → N-[2,6-bis(1-methylethyl)phenyl]-N'-(diphenylmethoxy)-urea

HRID 465995Notes

Reaction equation

HRID 465995 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[C:20]=1[N:28]=[C:29]=[O:30])([CH3:18])[CH3:17]>C(OCC)(=O)C>[CH3:18][CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[C:20]=1[NH:28][C:29]([NH:9][O:8][CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:30])[CH3:17]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 198860O-benzhydrylhydroxylamine

Product 1

HCID 11741848N-[2,6-bis(1-methylethyl)phenyl]-N'-(diphenylmethoxy)-ureaYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-diphenylmethoxyamine (0.9 g, 0.0045 mol) (E. L. Schumann, et al, Journal of Medicinal Chemistry, Volume 7, pages 329-334 (1964)) in 20 ml of ethyl acetate is added 2,6-diisopropylphenyl isocyanate (0.91 g, 0.0045 mol) and the reaction mixture is stirred for 20 hours at room temperature. The volatiles are removed under reduced pressure and the residue treated with 30 ml hexane-ethyl acetate (4:1). The precipitated solid is filtered and dried affording 1.45 g of N-[2,6-bis(1-methylethyl)phenyl]-N'-(diphenylmethoxy)-urea; mp 152°-154° C.

Workup

  1. customThe volatiles are removed under reduced pressure
  2. additionthe residue treated with 30 ml hexane-ethyl acetate (4:1)
  3. filtrationThe precipitated solid is filtered
  4. customdried

Sources & evidence

ORD record
ord-8aacda7c64674f3ba564ba806c540523
Source dataset
uspto-grants-1992_10
Patent number
US05155127

Reaction notes

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