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

HRID 1644767

Reaction equation

HRID 1644767 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-8d44449e1a8c41379451b80e62cd026b
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Linked notes

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