Hydrochloric Acid → HCID 178490030, compound

HRID 83935Notes

Reaction equation

HRID 83935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:24])([CH3:23])[C:9]([NH:11][NH:12][C:13](=[S:22])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=O)=[CH:4][C:3]=1[O:25][CH3:26].Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:13]([SH:22])=[N:12][N:11]=2)([CH3:24])[CH3:23])=[CH:4][C:3]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866622622-(2-(4-Chloro-3-methoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)hydrazine carbothioamide

Product 1

HCID 178490030HCID 178490030, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2-(2-(4-chloro-3-methoxyphenyl)-2-methylpropanoyl)-N-(4-fluorophenyl)-hydrazine carbothioamide (8.13 g, 0.02 mol) in 3N NaOH (270 mL) was heated at reflux 4 h with mechanical stirring. The reaction mixture was cooled to 5° C. and acidified with 5N HCl to pH=4. The resulting whited solids were collected by filtration, washed with diethyl ether and dried to give 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-4-(4-fluorophenyl)-4H-1,2,4-triazole-3-thiol (7.5 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ 7.23-7.21 (d, 1H), 6.95-6.91 (t, 2H), 6.54 (d, 1H), 6.52-6.49 (dd, 1H), 6.45-6.41 (m, 2H), 3.67 (s, 3H), 1.45 (s, 6H).

Workup

  1. temperatureat reflux 4 h with mechanical stirring
  2. filtrationThe resulting whited solids were collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-c507f5979700415cbaefa6b51b065ba2
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…