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

HRID 2225456Notes

Reaction equation

HRID 2225456 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.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[S:24](Cl)(=[O:26])=[O:25]>>[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:24]([C:20]1[S:19][CH:23]=[CH:22][CH:21]=1)(=[O:26])=[O:25])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

3

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 189580232-(2,4-Dichlorophenyl)-3-(2-thiophenesulfonamido)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

Procedure

Following the procedure described in the preceeding example but using 3-amino-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol and 2-thienylsulfonylchloride, the title compound was obtained in a similar yield: mp 169°-180° C.; 1H NMR (80 MHz, MeOH-d4)δ(TMS) 8.19 (s, 1H, CH=N), 7.74 (s, 1H, CH=N), 7.7-7.0 (m, 6H, arom), 4-95 (AB system, Δv=0.60, J=14.5 Hz, 2H, CH2 -Tr), 3.68 (AB system, Δv=0.13, J=14 Hz, 2H, CH2NH). Anal calcd. for C15H14Cl2N4O3S2 : C 41.58%; H 3.26%; N 12.93%. Found: C 42.39%; H 3.27%; N 13.06%.

Sources & evidence

ORD record
ord-369ed9ab7e5c4981a8e83d3957e3a71f
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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