2-Mesitylenesulfonyl chloride → 2-(2,4-Dichlorophenyl)-3-(2,4,6-trimethylbenzenesulfonamido)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2225452Notes

Reaction equation

HRID 2225452 reaction equation
[NH2:1][CH2:2][C:3]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])([OH:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28](Cl)(=[O:30])=[O:29]>>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:3]([OH:10])([CH2:2][NH:1][S:28]([C:21]1[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=1[CH3:19])(=[O:30])=[O:29])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

3

Reactant 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 189579752-(2,4-Dichlorophenyl)-3-(2,4,6-trimethylbenzenesulfonamido)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

Procedure

Following the procedure described in the preceeding examples but using 3-amino-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol and 2,4,6-trimethylbenzenesulfonylchloride, the title compound was obtained in a similar yield: mp 171°-172° C.; 1H NMR (80 MHz, CDCl3)δ(TMS) 7.94 (s, 1H, CH=N), 7.80 (s, 1H, CH=N), 7.68 (s, 4H, arom), 7.7-7.0 (m, 3H, arom), 6.88 (s, 2H, arom), 4.93 (AB system, Δv=0.32, J=14.5 Hz, 2H, CH2 -Tr), 3.7-3.3 (m, 2H, CH2NH), 2.54 (s, 6H, 2Me), 2.29 (s, 3H, Me). Anal calcd. for C20H22Cl2N4O3S: C 51.18%; H 4.72%; N 11.94%. Found: C 51.26%; H 4.98%; N 11.92%.

Sources & evidence

ORD record
ord-0578ba91b91640e8b1c93a2715a0125b
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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