Triethylamine → HCID 12669671, compound
Reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][NH:6][N:7]([CH3:18])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:9].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:5][N:6]1[C:1](=[S:2])[N:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8](=[O:9])[N:7]1[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3.8 g (0.033 mol) thiophosgene in 10 ml chloroform was added dropwise to a stirred solution of 7 g (0.033 mol) 1,2-dimethyl-4-(4-chlorophenyl)semicarbazide and 6.67 g (0.066 mol) triethylamine in 200 ml chloroform. After completion of the addition, the reaction mixture was heated under reflux for 2 hours and stirred at about 25° C. for 3 days. The reaction mixture was then washed with water, dilute hydrochloric acid solution, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 10 g of a semi-solid residue. The residue was diluted with 100 ml dichloromethane and filtered. The filtate was chromatographed on 200 g of silica gel. Elution with 1% methanol in dichloromethane gave the product, 3.9 g, as light tan crystals, m.p. 143°-144° C. Infrared analysis showed strong carbonyl absorption at 5.8 micron. The product is tabulated in Table I as Compound No. 2.
Workup
- additionAfter completion of the addition
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 2 hours
- washThe reaction mixture was then washed with water, dilute hydrochloric acid solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-2b518801a5524da592f2def0cb8f8dc5
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04276420
Reaction notes
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