Triethylamine → HCID 695624, compound

HRID 2081576Notes

Reaction equation

HRID 2081576 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.C(OC(Cl)=O)C.[NH2:26][C:27]1[C:28](=[O:34])[NH:29][C:30](=[O:33])[NH:31][CH:32]=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:26][C:27]2[C:28](=[O:34])[NH:29][C:30](=[O:33])[NH:31][CH:32]=2)=[O:10])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 136115-AminouracilHCID 26229(4-Chlorophenoxy)acetic acid

Product 1

HCID 695624HCID 695624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.87 g (0.01M) p-chlorophenoxyacetic acid is suspended with stirring in 30 ml dry dimethylformamide and dissolved by addition of 1. g (0.01M) triethylamine. The reaction mixture is cooled to 0° to 5° C. internal temperature, mixed with 1.1 g (0.1M) chloroformic acid ethyl ester and stirred one minute at its reaction temperature. To the reaction mixture of the mixed anhydrides one rapidly adds a solution of 1.27 g (0.01M) 5-aminouracil in dry dimethylformamide and stirs for 30 minutes. Subsequently the reaction mixture is poured into 1 liter ice water, the precipitate is filtered with suction, dried and recrystallized from water in the ratio 1:1.

Workup

  1. dissolutiondissolved by addition of 1
  2. temperatureThe reaction mixture is cooled to 0° to 5° C. internal temperature
  3. filtrationthe precipitate is filtered with suction
  4. customdried
  5. customrecrystallized from water in the ratio 1:1

Sources & evidence

ORD record
ord-714946abd5b84bf8a5ab3f9dd79442c9
Source dataset
uspto-grants-1993_02
Patent number
US05185341

Reaction notes

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