1-Propanesulfonyl chloride → 2-(2,4-Dichlorophenyl)-3-(propanesulfonamido)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2225454Notes

Reaction equation

HRID 2225454 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.[CH2:19]([S:22](Cl)(=[O:24])=[O:23])[CH2:20][CH3:21]>>[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:22]([CH2:19][CH2:20][CH3:21])(=[O:24])=[O:23])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

3

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 189580032-(2,4-Dichlorophenyl)-3-(propanesulfonamido)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

Procedure

Following the procedure described in example 1 but using 3-amino-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol and propanesulfonylchloride, the title compound was obtained in a similar yield: mp 128°-129° C.; 1H NMR (80 MHz, CDCl3)δ(TMS) 7.99 (s, 1H, CH=N), 7.83 (s, 1H, CH=N), 7.62 (d, J=8.5 Hz, 1H, arom), 7.4-7.1 (m, 2H, arom), 5.00 (AB system, Δv=0.56, J=14.5 Hz, 2H, CH2 -Tr), 4.91 (m, 1H, NH, 4.1-3.5 (m, 2H, CH2NH), 3.1-2.8 (m, 2H, CH2S), 2.1-1.5 (m, 2H, CH2CH2S), 1.00 (t, J=7.5 Hz, 3H, Me). Anal calcd. for C14H18Cl2N4O3S: C 42.76%; H 4.61%; N 14.25%. Found: C 42.61%; H 4.77%; N 14.08%.

Sources & evidence

ORD record
ord-49079fefff074083b8d09e42177f4df6
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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