2-Acetamido-1,3-thiazole-5-sulfonyl chloride → 3-(2-Acetamido-5-thiazolesulfonamido)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

HRID 2225457Notes

Reaction equation

HRID 2225457 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.[C:19]([NH:22][C:23]1[S:24][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:26][N:27]=1)(=[O:21])[CH3:20]>>[C:19]([NH:22][C:23]1[S:24][C:25]([S:28]([NH:1][CH2:2][C:3]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])([OH:10])[CH2:4][N:5]2[CH:9]=[N:8][CH:7]=[N:6]2)(=[O:29])=[O:30])=[CH:26][N:27]=1)(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chlorideHCID 147065211-[3-Amino-2-(2,4-dichlorophenyl)-2-hydroxyprop-1-yl]-1H-1,2,4-triazole

Product 1

HCID 189580153-(2-Acetamido-5-thiazolesulfonamido)-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 3-amino-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol and 2-acetamido-5-thiazolesulfonylchloride, the title compound was obtained in a similar yield: mp 96°-112° C.; 1H NMR (80 MHz, MeOH-d4)δ(TMS) 8.27 (s, 1H, CH=N), 7.74 (s, 1H, CH=N), 7.55 (d, J=8.5 Hz, 1H, arom), 7.3-7.1 (m, 2H, arom), 4.80 (AB system, Δv=0.35, J=14.5 Hz, 2H, CH2 -Tr), 3.74 (AB system, Δv=0.36, J=13.8Hz, 2H, CH2NH), 2.37 (s, 1H, Me), 2.22 (s, 1H, Me). Anal calcd. for C17H18Cl2N6O4S2 : C 40.40%; H 3.59%; N 16.63%. Found: C 40.69%; H 4.06%; N 16.70 %.

Sources & evidence

ORD record
ord-514a39e323da47559be1fa22141ea0de
Source dataset
uspto-grants-1994_09
Patent number
US05344839

Reaction notes

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