Triethylamine → 4-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

HRID 341274Notes

Reaction equation

HRID 341274 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][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][C:8]([C:11](=[O:12])[NH:28][C:26]2[S:27][C:23]([S:22][CH3:21])=[CH:24][N:25]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3516785-(Methylthio)thiazol-2-amineHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 575718204-{[5-(Methylsulfanyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetateYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the procedure for the synthesis of example 82, intermediate 510 (0.815 g, 4.10 mmol) dissolved in dry THF (25.0 mL), triethylamine (0.572 mL, 4.10 mmol), and 512 (0.500 g, 3.42 mmol) dissolved in dry THF (10.0 mL) gave 76 (0.887 g, 84%) as a tan solid.

Sources & evidence

ORD record
ord-95dbee9ee0664515948d094a26897604
Source dataset
uspto-grants-2014_11
Patent number
US08895752B2

Reaction notes

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