1-Butanesulfonyl chloride → 3-Butanesulfonamido-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2225455Notes

Reaction equation

HRID 2225455 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:23](Cl)(=[O:25])=[O:24])[CH2:20][CH2:21][CH3:22]>>[CH2:19]([S:23]([NH: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)(=[O:25])=[O:24])[CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 754301-Butanesulfonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 537485493-Butanesulfonamido-2-(2,4-dichlorophenyl)-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 butanesulfonylchloride, the title compound was obtained in a similar yield as a solid foam: 1H NMR (80 MHz, CDCl3)δ(TMS) 8.00 (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), 4.88 (t, J=6.4 Hz, 1H, NH), 4.1-3.5 (m, 2H, CH2NH), 3.1-2.8 (m, 2H, NCH2CH2), 1.8-1.1 (m, 4H, NCH2CH2CH2), 1.1-0.7 (m, 3H, CH3). Anal calcd. for C15H20Cl2N4O3S: C 44.23%; H 4.95%; N 13.76%. Found: C 44.80%; H 5.37%; N 13.16%.

Sources & evidence

ORD record
ord-21aeefbe51df40a6aaa878f818bec642
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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