Triethylamine → N-[(5-ethyl-4-phenyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

HRID 1009048Notes

Reaction equation

[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.Cl[C:12](OC1C=CC=CC=1)=[O:13].C(N(CC)CC)C.[CH2:28]([C:30]1[S:34][C:33]([NH2:35])=[N:32][C:31]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:29]>C(#N)C>[CH2:28]([C:30]1[S:34][C:33]([NH:35][C:12]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:13])=[N:32][C:31]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:29]

Participants

Conditions

Temperature: 57.5 °C

Procedure

5-Methyl-thiophene-3-sulfonic acid amide (0.0789 g, 0.445 mmol) was dissolved in 4 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.0697 g, 1.00 eq.) and triethylamine (0.154 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1. h. The above prepared 5-ethyl-4-phenyl-thiazol-2-ylamine (0.0910 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 55-60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/ethyl acetate=1/1), yielded 0.081 g of the title compound as off-white crystals.

Workup

customkept at ambient temperature for 1
additionwas then added
temperatureCooling
additionpouring
extractionice/NH4Cl, twofold extraction with ethyl acetate
washwashing with brine
dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record: ord-4c87d02e34514f519f333aece362af33
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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