Aniline → HCID 19106876, compound
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)=[S:4].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>ClC(Cl)C.O.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[S:4]Participants
Conditions
- Temperature
- 25 °C
Procedure
A stirred suspension of (±)-N-methyl-2-oxo-1-(3-pyridyl)cyclohexanecarbothioamide (2.5 g) and aniline (3.72 g) in anhydrous dichloroethane (30 ml) under an argon atmosphere was treated dropwise at 25° C. with titanium tetrachloride (0.8 ml). The reaction mixture was stirred at 25° C. until completion of the reaction (as judged by TLC analysis), and then it was poured into a solution of sodium bicarbonate (16.8 g) in water (100 ml) and stirred for 15 minutes. The mixture was filtered through a pad of celite and the aqueous layer was extracted with dichloromethane (3×75 ml). The combined organic solution was washed with aqueous sodium bicarbonate solution (100 ml; 10% w/w), with water (50 ml) and with saturated brine (100 ml), and then it was dried over sodium sulphate and concentrated in vacuo, to give N-methyl-2-phenylimino-1-(3-pyridyl)cyclohexanecarbothioamide in the form of a crude oil.
Workup
- stirringstirred for 15 minutes
- filtrationThe mixture was filtered through a pad of celite
- extractionthe aqueous layer was extracted with dichloromethane (3×75 ml)
- washThe combined organic solution was washed with aqueous sodium bicarbonate solution (100 ml; 10% w/w), with water (50 ml) and with saturated brine (100 ml)
- dry with materialit was dried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bc373f1d00eb465d86eb165d08ac296c
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05276045
Reaction notes
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