Triethylamine → HCID 20154303, compound

HRID 2413896Notes

Reaction equation

HRID 2413896 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[S:8][C:9]([CH2:12][NH2:13])=[CH:10][CH:11]=2)[N:6]=1.C(N(CC)CC)C.[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[S:8][C:9]([CH2:12][NH:13][C:26](=[O:27])[CH2:25][O:24][C:21](=[O:23])[CH3:22])=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 20154278HCID 20154278, compound

Product 1

HCID 20154303HCID 20154303, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-amino-4-(5-aminomethyl-2-thienyl) thiazole in 150 ml of chloroform is added 10 ml of triethylamine, and 3.1 g of acetoxyacetylchloride is added dropwise with stirring at room temperature (10°-35° C.). The whole mixture is stirred at room temperature for an hour, and then washed with water. The organic layer is separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is recrystallized from ethanol to give 2-amino-4-(5-acetoxyacetylaminomethyl-2-thienyl) thiazole, melting at 149°-150° C. The corresponding maleate melts at 153°-154° C. with decomposition.

Workup

  1. additionis added dropwise
  2. stirringThe whole mixture is stirred at room temperature for an hour
  3. washwashed with water
  4. customThe organic layer is separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-69ef727b6cb54d4abd86a08b82df35de
Source dataset
uspto-grants-1988_01
Patent number
US04720493

Reaction notes

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