Dichloromethane → 3-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amine

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.C[CH2:14][N:15]([CH:19](C)C)C(C)C.ClN1C=C(Cl)[S:25][NH:24]1.C(Cl)[Cl:30]>>[Cl:30][C:19]1[N:15]=[C:14]([NH:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([CH3:12])[CH3:11])[S:25][N:24]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 81531Diisopropylethylamine

HCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

HCID 866736213,5-Dichlorothiadiazole

Product 1

HCID 709750603-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amineYield 94%

Procedure

To a 0° C. solution of 2-(4-fluorophenyl)-2-methylpropan-1-amine (16.8 g, 101 mmol, 1.0 equiv) and DIPEA (35 mL, 200 mmol, 2.0 equiv) in dry DCM (350 mL) was slowly added 3,5-dichlorothiadiazole (15.5 g, 101 mmol, 1.0 equiv). The reaction was allowed to stir at room temperature until starting material was consumed as judged by HPLC/MS. The reaction was diluted with water and EtOAc. The layers were separated, and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a yellow-orange oil (27 g, 94%). m/z=284.1 [M+H]+.