tert-Butyl isocyanate → HCID 54465920, compound

HRID 328470Notes

Reaction equation

HRID 328470 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[NH:4][C:5](=[NH:8])[O:6][CH3:7].[C:11]([N:15]=[C:16]=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[CH3:1][N:2]([CH3:10])[C:3]([N:4]=[C:5]([O:6][CH3:7])[NH:8][C:16]([NH:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])=[O:9]

Participants

3

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 152773082HCID 152773082, compound

Product 1

HCID 54465920HCID 54465920, compound

Procedure

5 Parts of methyl 4,4-dimethylallophanimidate and 20 ml of t-butylisocyanate are refluxed overnight. The next day, the solution is evaporated to give an oil, which crystallizes when tirturated with petroleum-ether under cooling. In order to remove some unreacted starting material and byproducts, the solids are first triturated with water and filtered. After drying, the solids are then triturated with carbon tetrachloride and impurities removed by filtration. The carbon tetrachloride filtrate is then evaporated and the residue recrystallized from petroleum-ether to give pure methyl N-dimethylcarbamoyl-4-t-butylallophanimidate (a compound of Formula I), m.p. 96°-98° C.

Workup

  1. customThe next day, the solution is evaporated
  2. customto give an oil, which
  3. customcrystallizes when
  4. temperatureunder cooling
  5. customIn order to remove
  6. customthe solids are first triturated with water
  7. filtrationfiltered
  8. customAfter drying
  9. customthe solids are then triturated with carbon tetrachloride and impurities
  10. customremoved by filtration
  11. customThe carbon tetrachloride filtrate is then evaporated
  12. customthe residue recrystallized from petroleum-ether

Sources & evidence

ORD record
ord-279a6530cc8243d4b65064c41fcad08d
Source dataset
uspto-grants-1977_04
Patent number
US04017529

Reaction notes

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