4-(TOLUENE-4-SULFONYLMETHYL)-THIAZOL-2-YLAMINE → HCID 25141449, compound

HRID 2068006Notes

Reaction equation

[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:22][N:23]=[C:24]=[O:25]>C1COCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:22][NH:23][C:24]([NH:16][C:13]1[S:14][CH:15]=[C:11]([CH2:10][S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[N:12]=1)=[O:25]

Participants

Conditions

Temperature: 150 °C

Procedure

4-(Toluene-4-sulfonylmethyl)-thiazol-2-ylamine (0.5 mmol) was dissolved in THF (3 ml) and 3,4-dichlorobenzylisocyanate (1.2 eq., 0.6 mmol) was added. The reaction was heated by microwave for 30 min. at 150° C. Solvent was removed in vacuo. The crude product was purified by column chromatography eluting with a gradient of 0-20% EtOAc (with 10% MeOH) in hexanes to give the title compound as a white solid in 66% yield.

Workup

customSolvent was removed in vacuo
customThe crude product was purified by column chromatography
washeluting with a gradient of 0-20% EtOAc (with 10% MeOH) in hexanes

Sources & evidence

ORD record: ord-fde822abe8504bde837993ac0d4cc2a1
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293919B2

Reaction notes

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