3,5-Dichloro-2-hydroxybenzenesulphonyl chloride → 3-(3,5-Dichloro-2-hydroxybenzenesulfonamido)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2225451Notes

Reaction equation

HRID 2225451 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:16][NH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[Cl:19][C:20]1[C:21]([OH:31])=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:23]=[C:24]([Cl:26])[CH:25]=1>>[Cl:19][C:20]1[C:21]([OH:31])=[C:22]([S:27]([NH:17][CH2:16][C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])([OH:18])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)(=[O:29])=[O:28])[CH:23]=[C:24]([Cl:26])[CH:25]=1

Participants

3

Reactant 2

HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 189579723-(3,5-Dichloro-2-hydroxybenzenesulfonamido)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

Procedure

Following the procedure described in the preceeding examples but using 2-(2,4-dichlorophenyl)-3-amino-1-(1H-1,2,4-triazol-1-yl)propan-2-ol and 3,5-dichloro-2-hydroxybenzenesulfonylchloride, the title compound was obtained in a similar yield: mp dec; 1H NMR (80 MHz, MeOH-d4)δ(TMS) 8.4-8.1 (m, arom), 7.7-7.4 (m, CH=N, arom), 7.3-7.0 (m, arom), 4.76 (AB system, Δv=0.35, J=14.5 Hz, 2H, CH2 -Tr), 3.81 (AB system, Δv=0.72, J=14 Hz, 2H, CH2NH). Anal calcd. for C17H14Cl4N4O4S: C 39.87%; H 2.76%; N 10.94%. Found: C 39.75%; H 2.96%; N 10.90%.

Sources & evidence

ORD record
ord-601c64183cdc468dbd2716b9cfe31acc
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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