Triethylamine → HCID 13150546, compound

HRID 462329Notes

Reaction equation

HRID 462329 reaction equation
[OH:1][N:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([NH:5][C:6]1[S:10][N:9]=[N:8][CH:7]=1)=[O:4].C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>O1CCCC1>[C:11]1([N:2]([O:1][C:24](=[O:27])[CH2:25][CH3:26])[C:3]([NH:5][C:6]2[S:10][N:9]=[N:8][CH:7]=2)=[O:4])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 13150545HCID 13150545, compound

Product 1

HCID 13150546HCID 13150546, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

9.43 g (0.04 mole) 1-hydroxy-1-phenyl-3-(1,2,3-thiadiazole-5-yl)-urea were under addition of 6.15 ml (0.044 mole) triethylamine dissolved in 100 ml tetrahydrofuran. There were added to this solution under cooling to 20° C., a solution of 3.46 ml (0.04 mole) propionylchloride in 10 ml tetrahydrofuran within about 5 minutes in dropwise fashion and thereafter the resulting mixture was stirred for an hour. After separating off the precipitate which had formed the filtrate was concentrated and the residue taken up in 150 ml of ether. The ether phase was washed with water, dried over magnesium sulfate, again concentrated and the residue digested with diisopropylether.

Workup

  1. additionThere were added to this solution
  2. customAfter separating off the precipitate which
  3. customhad formed the filtrate
  4. concentrationwas concentrated
  5. washThe ether phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationagain concentrated

Sources & evidence

ORD record
ord-8c04b739c9f14ef59fa8b84df02ab8b9
Source dataset
uspto-grants-1985_05
Patent number
US04515619

Reaction notes

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