Triethylamine → 3-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

HRID 1620885Notes

Reaction equation

HRID 1620885 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](Cl)=[O:12])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22][C:23]1[S:27][C:26]([NH2:28])=[N:25][CH:24]=1>C1COCC1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:12])[NH:28][C:26]2[S:27][C:23]([S:22][CH3:21])=[CH:24][N:25]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3516785-(Methylthio)thiazol-2-amineHCID 129985583-(Chlorocarbonyl)phenyl acetate

Product 1

HCID 575718763-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the procedure for the synthesis of example 513, intermediate 511 (0.815 g, 4.10 mmol) dissolved in dry THF (25.0 mL), triethylamine (0.572 mL, 4.10 mmol), and 514 (0.500 g, 3.42 mmol) dissolved in dry THF (10.0 mL) gave 516 (0.681 g, 65%) as a tan solid.

Sources & evidence

ORD record
ord-acdffc5848f147dba3b3f813f0823593
Source dataset
uspto-grants-2014_07
Patent number
US08772502B2

Reaction notes

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