Imidazole → HCID 14327496, compound

HRID 1706679Notes

Reaction equation

HRID 1706679 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[NH:4][C:5](=O)[CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH3:11].C(N(CC)CC)C.C(Cl)(Cl)=O.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[N:4]=[C:5]([N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1)[CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6371PhosgeneHCID 8471TriethylamineHCID 20333993HCID 20333993, compound

Product 1

HCID 14327496HCID 14327496, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.9 g of 2',4'-dichloro-3-(propoxy)propionanilide and 8 g of triethylamine were dissolved in 30 ml of chloroform and 3.7 g of phosgene were introduced thereto at 0° to 10° C. under cooling with ice. After raising the temperature of the solution to room temperature, the solution was stirred for 2 hours, and then, 2 g of imidazole were added thereto. The mixture was heated under reflux for 2 hours. After completion of the reaction, the resulting reaction solution was cooled to room temperature, washed with water and dried over anhydrous magnesium sulfate. Removal of chloroform from the solution by distillation gave 7.7 g of the desired compound. (nD29 1.5688)

Workup

  1. temperatureat 0° to 10° C. under cooling with ice
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter completion of the reaction
  5. customthe resulting reaction solution
  6. temperaturewas cooled to room temperature
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customRemoval of chloroform from the solution
  10. distillationby distillation

Sources & evidence

ORD record
ord-98daab31321446bebb9f21b96876f5b0
Source dataset
uspto-grants-1980_06
Patent number
US04208411

Reaction notes

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