Water → HCID 136123886, compound

HRID 904163Notes

Reaction equation

HRID 904163 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[N:8][C:9](=[O:11])O.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH3:21])[CH3:20])=[N:17][CH:18]=1.O>CN(C=O)C>[CH3:20][N:19]([CH3:21])[C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:9]([N:8]=[C:3]2[NH:4][C:5](=[O:7])[CH2:6][N:2]2[CH3:1])=[O:11])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78642N2,N2-dimethylpyridine-2,5-diamineHCID 136469822tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene carbamic acid

Product 1

HCID 136123886HCID 136123886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.1 g (35 mM) of the phenyl carbamate 8 and 2.5 g (23 mM) of 5-amino-2-dimethylaminopyridine in 50 ml of anhydrous DMF was heated at 55° for 3.5 hrs. and then cooled and poured into 200 ml of water. The resulting mixture was extracted with three 100 ml portions of ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated to a volume of 50 ml. The precipitate which formed was collected and recrystallized from acetone to give 0.84 of the above urea as tan crystals, m.p. 212°-213° C.

Workup

  1. temperaturewas heated at 55° for 3.5 hrs
  2. temperatureand then cooled
  3. extractionThe resulting mixture was extracted with three 100 ml portions of ethyl acetate
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of 50 ml
  7. customThe precipitate which formed
  8. customwas collected
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-441723659bf543b4808740c696b2eb3c
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

Loading…