4-Chlorophenyl isothiocyanate → N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide

HRID 1023161Notes

Reaction equation

[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15])[CH:8]=2)[NH:3]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1>CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:17][NH:16][C:14](=[O:15])[CH2:13][O:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH2:11][CH2:10]3)=[S:27])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetohydrazide (0.2 g, 0.85 mmol) in dry DMF (5 mL) at room temperature, 1-chloro-4-isothiocyanatobenzene (0.158 mg, 0.93 mmol) was added and the reaction was heated at 60° C. overnight. The reaction was monitored by LCMS. Solvent was removed under vacuum, then water (10 mL) was added to the residue. The solid was filtered and dried to yield crude N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide (0.250 mg, 73%). LCMS: RT 1.39 min. LCMS (ES-API), m/z 405.0 (M+H).

Workup

customSolvent was removed under vacuum
additionwater (10 mL) was added to the residue
filtrationThe solid was filtered
customdried

Sources & evidence

ORD record: ord-f308985f6959477999547fbe9abacaab
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722670B2

Reaction notes

Loading…