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

HRID 1620884Notes

Reaction equation

HRID 1620884 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 512, intermediate 510 (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 515 (0.887 g, 84%) as a tan solid.

Sources & evidence

ORD record
ord-19a1d533aa6c4c6ebc50139a9e92ad9e
Source dataset
uspto-grants-2014_07
Patent number
US08772502B2

Reaction notes

Loading…