tert-Butyl isocyanate → 1-tert-butyl-3-[N-(2,6-dimethylphenyl)-N-methylcarbamimidoyl]urea

HRID 2398831Notes

Reaction equation

HRID 2398831 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH3:13])[C:10]([NH2:12])=[NH:11].[C:14]([N:18]=[C:19]=[O:20])([CH3:17])([CH3:16])[CH3:15]>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH3:13])[C:10]([NH:12][C:19]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])=[NH:11]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 204344741-(2,6-Dimethylphenyl)-1-methylguanidine

Product 1

HCID 1403273821-tert-butyl-3-[N-(2,6-dimethylphenyl)-N-methylcarbamimidoyl]urea

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a mixture of 8.7 g. (0.05 mole) of 1-(2,6-dimethylphenyl)-1-methylguanidine and 10 ml. xylene is added 5 g. of t-butylisocyanate (0.05 mole) and the mixture is refluxed for 2 hours. The reaction product is cooled, triturated with heptane and filtered. Recrystallization from 1:1 isopropanol/water results in 1-(2,6-dimethylphenyl-N-methylamidino)-3-(t-butyl)urea.

Workup

  1. additionTo a mixture of 8.7 g
  2. temperatureThe reaction product is cooled
  3. customtriturated with heptane
  4. filtrationfiltered
  5. customRecrystallization from 1:1 isopropanol/water
  6. customresults in 1-(2,6-dimethylphenyl-N-methylamidino)-3-(t-butyl)urea

Sources & evidence

ORD record
ord-2bdf7a2321ec4b5cb3bbfa955524cf33
Source dataset
uspto-grants-1977_05
Patent number
US04025652

Reaction notes

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