Triethylamine → N,N'-diheptyl-S-ethyl-N-propane sulfonyl isothiourea
Reaction equation
C(N(CC)CC)C.[CH2:8]([NH:15][C:16](=[N:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[S:17][CH2:18][CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:28]([S:31](Cl)(=[O:33])=[O:32])[CH2:29][CH3:30]>C(Cl)Cl>[CH2:21]([N:20]([S:31]([CH2:28][CH2:29][CH3:30])(=[O:33])=[O:32])[C:16](=[N:15][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:17][CH2:18][CH3:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.8 g (0.018 mole) of triethylamine was added to 4.5 g (0.015 mole) N,N'-diheptyl-S-ethyl-isothiourea in 50 ml methylene chloride in a stirred round bottom flask. A solution of propanesulfonyl chloride (0.018 mole, 2.6 g) in 8 ml methylene chloride was added dropwise to the above solution at 0° C. The mixture was stirred 1.5 hours at room temperature then at 30°-35° C. for 1.5 hours. The cooled solution was washed twice with 20 ml water, once with 25 ml saturated sodium bicarbonate solution and twice more with 20 ml of water. The organic phase was dried over magnesium sulfate and evaporated invacuo to yield the product as a yellow oil. nD30 1.4805. Yield was 5.2 g (85.4% of theory). The structure was confirmed by IR spectrum. Compound No. 203 in Table I.
Workup
- waitat 30°-35° C. for 1.5 hours
- washThe cooled solution was washed twice with 20 ml water, once with 25 ml saturated sodium bicarbonate solution and twice more with 20 ml of water
- dry with materialThe organic phase was dried over magnesium sulfate
- customevaporated invacuo
Sources & evidence
- ORD record
- ord-5ea2983ce71e40aa80f43d2239cfb9e0
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04357351
Reaction notes
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