tert-Butyl isocyanate → HCID 178440907, compound

HRID 2410018Notes

Reaction equation

HRID 2410018 reaction equation
[CH3:1][C:2]([N:5]1[C:10](=[O:11])[CH2:9][C:8](=[O:12])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[C:6]1=[O:24])([CH3:4])[CH3:3].C([N:29]=[C:30]=[O:31])(C)(C)C.C(C1C=CC(CN)=CC=1)(C)(C)C.Cl[C:45](Cl)([C:49]([O-:51])=[O:50])C([O-])=O>ClCCl>[CH3:4][C:2]([N:5]1[C:10]([OH:11])=[C:9]([C:30]([NH:29][CH2:45][C:49]([OH:51])=[O:50])=[O:31])[C:8](=[O:12])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[C:6]1=[O:24])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 62412tert-Butyl isocyanateHCID 27356554-tert-ButylbenzylamineHCID 17924345HCID 17924345, compoundHCID 68637037HCID 68637037, compound

Product 1

HCID 178440907HCID 178440907, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1,1-Dimethylethyl)-3-{[4-(1,1-dimethylethyl)phenyl]methyl}-2,4,6(1H,3H,5H)-pyrimidinetrione. A mixture of t-butyl isocyanate (571 uL, 5.0 mmoles) and 4-t-butylbenzylamine (880 uL, 5.0 mmoles) in dry dichloromethane was stirred for 1 hour. Dichloromalonate (486 uL, 5.0 mmoles) was added and the mixture was heated under reflux for 1 hour. The mixture was washed with 1N hydrochloric acid and evaporated onto silica gel. Flash chromatography (10-35% ethyl acetate-hexane) gave the title compound (1.3 g, 79%) 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (s, 9 H) 1.63 (s, 9 H) 3.60 (s, 2 H) 4.99 (s, 2 H) 7.37 (d, J=2.78 Hz, 4 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. washThe mixture was washed with 1N hydrochloric acid
  4. customevaporated onto silica gel

Sources & evidence

ORD record
ord-2557e4aac9134097a446a3de1d082dec
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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