Water → HCID 4564557, compound

HRID 987066Notes

Reaction equation

HRID 987066 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[NH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.C(N(CC)CC)C.O>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 752462-Naphthoyl chloride

Product 1

HCID 4564557HCID 4564557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.7 g (24.9 mmol) of 2-naphthoyl chloride, dissolved in 50 ml of anhydrous tetrahydrofuran, were added dropwise at 0° C. to 4 g (23.3 mmol) of ethyl 2-aminothiazole-4-carboxylate and 6.4 ml (46.5 mmol) of triethylamine in 150 ml of anhydrous tetrahydrofuran. The entire mixture was then stirred for 16 h. The reaction solution was then poured into plenty of water and extracted with ethyl acetate. The organic phase was then washed with aqueous sodium hydrogencarbonate solution, dried and concentrated in vacuo. The residue was purified by chromatography (eluent: methylene chloride), 5.6 g (82%) of the product being obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was then washed with aqueous sodium hydrogencarbonate solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (eluent: methylene chloride), 5.6 g (82%) of the product
  6. custombeing obtained

Sources & evidence

ORD record
ord-70e223bf01fb4cb49395a9a723e6d115
Source dataset
uspto-grants-2003_10
Patent number
US06630493B1

Reaction notes

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