Methyl chloroformate → 1-Methyl-4,5-dihydro-5-phenyl-2-methoxycarbonylaminoimidazole

HRID 372036Notes

Reaction equation

HRID 372036 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].Br.[CH3:7][N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][N:10]=[C:9]1[NH2:19].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:7][N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][N:10]=[C:9]1[NH:19][C:2]([O:4][CH3:5])=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 20353087HCID 20353087, compound

Product 1

HCID 232745111-Methyl-4,5-dihydro-5-phenyl-2-methoxycarbonylaminoimidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This example illustrates another process embodiment of the invention wherein an alkyl chloroformate is used as one of the reagents. In the example, 0.8 g. of methyl chloroformate is added over a five minute period to a stirring mixture of 2 g. 1-methyl-2-amino-5-phenyl-2-imidazoline hydrobromide, 1.4 g. sodium bicarbonate, and 20 ml. acetone held at 0° C. After addition is complete, the mixture is allowed to warm to room temperature and then stirred for 16 hours at room temperature. The mixture is distilled to a low volume and 50 ml. of water is then added. The mixture is filtered and the precipitate collected and washed with water and then dried affording 1-methyl-4,5-dihydro-5-phenyl-2-methoxycarbonylaminoimidazole which is then further purified by recrystallization from chloroform.

Workup

  1. customheld at 0° C
  2. additionAfter addition
  3. distillationThe mixture is distilled to a low volume and 50 ml
  4. additionof water is then added
  5. filtrationThe mixture is filtered
  6. customthe precipitate collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-039643ccdf344c04b1623917a4d0f00d
Source dataset
uspto-grants-1978_05
Patent number
US04088771

Reaction notes

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