2-Hydrazinyl-6-methoxy-1,3-benzothiazole → 5-(4-Chlorophenyl)-3-(3-hydroxypropyl)-1-(6-methoxy-2-benzothiazolyl)pyrazole

HRID 5014Notes

Reaction equation

HRID 5014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.[NH:17]([C:19]1[S:20][C:21]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=2[N:23]=1)[NH2:18]>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]([C:19]3[S:20][C:21]4[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=4[N:23]=3)[N:18]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 19878462-Hydrazinyl-6-methoxy-1,3-benzothiazoleHCID 144974141-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione

Product 1

HCID 197975645-(4-Chlorophenyl)-3-(3-hydroxypropyl)-1-(6-methoxy-2-benzothiazolyl)pyrazoleYield 80.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

6-(4-Chlorophenyl)-4,6-diketohexanol (14.43 g, 60 mM) was treated with 2-hydrazino-6-methoxybenzothiazole (11.72 g, 60 mM) in pyridine (10 ml) and MeOH (300 ml) at reflux for 72 hr. Work-up as described in Example 1 followed by recrystallization from MeOH afforded the title compound 6 as a white solid (19.4 g), mp=123°-125° C.; NMR(CDCl3) δ 6.3 (s, 1H, C4 -H); MS, m/e 399 (M+).

Workup

  1. temperatureat reflux for 72 hr
  2. customfollowed by recrystallization from MeOH

Sources & evidence

ORD record
ord-c264e2331d7b4273ae53b165f3a42301
Source dataset
uspto-grants-1993_09
Patent number
US05242940

Reaction notes

Loading…