Water → HCID 23296364, compound

HRID 1954189Notes

Reaction equation

HRID 1954189 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.C(N(CC)CC)C.[C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])#[N:21].O>O1CCCC1>[C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=[O:26])#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 16495520Ethyl 2-aminothiazole-4-carboxylate hydrobromide

Product 1

HCID 23296364HCID 23296364, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 15 ml of dried tetrahydrofuran, 968 mg of 2-amino-4-ethoxycarbonyl-1,3-thiazolehydrobromide were suspended. To the suspension, 1.19 g of triethylamine were added. A solution of 3-cyanobenzoyl chloride dissolved in 3 ml of dried tetrahydrofuran was added dropwise to the resulting mixture under ice cooling, followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1), whereby 980 mg of 2-[N-(3-cyanobenzoyl)amino]-4-ethoxycarbonyl-1,3-thiazole were obtained as white crystals. Yield: 83%.

Workup

  1. additionwas added dropwise to the resulting mixture under ice cooling
  2. extractionthe resulting mixture was extracted with chloroform
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-5208db1f81ba443b8d49f409879eabb2
Source dataset
uspto-grants-2000_09
Patent number
US06121301

Reaction notes

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