Triethylamine → HCID 20240709, compound

HRID 746116Notes

Reaction equation

HRID 746116 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[Cl:12][C:13]1[C:14]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=2)=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[CH3:11][N:5]1[C:6](=[O:7])[CH:8]([C:28](=[O:29])[NH:27][C:24]2[CH:23]=[CH:22][C:21]([O:20][C:14]3[C:13]([Cl:12])=[CH:18][C:17]([Cl:19])=[CH:16][N:15]=3)=[CH:26][CH:25]=2)[C:9](=[O:10])[N:2]([CH3:1])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69860Dimethylbarbituric acidHCID 13686593HCID 13686593, compound

Product 1

HCID 20240709HCID 20240709, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

7.8 g (0.05 mol) of 1,3-dimethylbarbituric acid and 14 g (0.05 mol) of 4-(3,5-dichloropyrid-2-yloxy)phenylisocyanate are suspended in 50 ml of xylene. 1 g of triethylamine is added dropwise to the suspension and the temperature rises to 45°-50° C. After further addition of 50 ml of xylene the mixture is stirred for 18 hours at this temperature. Then 1/3 of the xylene is distilled off. After cooling, the precipitate is isolated by filtration, washed with xylene, suspended several times in HCl and the suspension is thoroughly washed with water and dried, affording 1,3-dimethyl-5-[4-(3,5-dichloropyrid-2-yloxy)phenylcarbamoyl]barbituric acid of the formula ##STR25## with a melting point of 234°-235° C.

Workup

  1. customrises to 45°-50° C
  2. distillationThen 1/3 of the xylene is distilled off
  3. temperatureAfter cooling
  4. customthe precipitate is isolated by filtration
  5. washwashed with xylene
  6. washthe suspension is thoroughly washed with water
  7. customdried

Sources & evidence

ORD record
ord-73f3118551f444689179a855e236d2dc
Source dataset
uspto-grants-1986_07
Patent number
US04602912

Reaction notes

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