Acetone → HCID 10566582, compound
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([NH2:10])[S:9][C:5]=2[CH:4]=1.Cl[CH2:16][CH2:17][S:18][CH2:19][CH2:20]Cl.CC(CC)=O.CC(C)=O>C(OCC)(=O)C>[NH:10]=[C:8]1[N:7]([CH2:16][CH2:17][S:18][CH2:19][CH3:20])[C:6]2[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:4][C:5]=2[S:9]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
2-Imino-3(2-ethylthioethyl)-6-trifluoromethylbenzothiazoline can be obtained in the following manner: A mixture of 6-trifluoromethyl-2-benzothiazolamine (32.3 g), 2-chloroethylsulphide (18 cc) and methylethylketone (20 cc) is heated under reflux for 16 hours. After cooling to 20° C., acetone (20 cc) is added and the solution obtained is poured into a mixture of ethyl acetate (200 cc) and petroleum ether (40°-60° C., 200 cc). The precipitate obtained is filtered off, taken up in water, and made alkaline with 28% ammonia. The base is then extracted with a mixture of ethylacetate (150 cc) and cyclohexane (150 cc) and purified on a column of silica (600 g), eluting with a mixture of ethylacetate and cyclohexane (50:50 by volume). 2-Imino-3-(2-ethylthioethyl)-6-trifluoromethylbenzothiazoline (33.2 g), m.p. 50° C., is thus obtained.
Workup
- temperatureis heated
- temperatureunder reflux for 16 hours
- customthe solution obtained
- customThe precipitate obtained
- filtrationis filtered off
- extractionThe base is then extracted with a mixture of ethylacetate (150 cc) and cyclohexane (150 cc)
- custompurified on a column of silica (600 g)
- washeluting with a mixture of ethylacetate and cyclohexane (50:50 by volume)
Sources & evidence
- ORD record
- ord-1bcf6bb866234f5d954469f733b4280c
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05008280
Reaction notes
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