Aniline → N-p-methylphenylsulfonyl-L-proline anilide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:18][CH2:17][CH2:16][C@H:12]2[C:13](O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.C1(N=C=NC2CCCCC2)CCCCC1.N[C:42]1C=CC=CC=1.[C:48](OCC)(=[O:50])C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:48](=[O:50])[C@@H:24]2[CH2:25][CH2:23][CH2:22][NH:21]2)[C:18]2[CH:17]=[CH:16][CH:12]=[CH:13][CH:42]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1Participants
Procedure
In this example, 8.07 g of N-p-methylphenylsulfonyl-L-proline and 3.03 g of triethylamine are dissolved in 100 ml ethyl acetate, and then dicyclohexyl carbodiimide (DCC; 6.18 g) is added thereto under ice cooling (5°-10° C.). The mixture is stirred for 20 minutes. After addition of 2.79 g aniline, the mixture is subjected to reaction at room temperature overnight with stirring. The deposited precipitate is filtered off, and the filtrate is washed three times with 100 ml water, twice with 100 ml 1N HCl, and then three times with 100 ml water. After drying over anhydrous sodium sulfate (about 30 g), the filtrate is concentrated under reduced pressure, and recrystallized from ethyl acetate-n-hexane (2:1 by volume), whereby N-p-methylphenylsulfonyl-L-proline anilide (compound number 18; 4.9 g; m.p. 140° C.) is obtained. Yield: 47.5%.
Workup
- customunder ice cooling (5°-10° C.)
- customthe mixture is subjected to reaction at room temperature overnight
- stirringwith stirring
- filtrationThe deposited precipitate is filtered off
- washthe filtrate is washed three times with 100 ml water
- dry with materialAfter drying over anhydrous sodium sulfate (about 30 g)
- concentrationthe filtrate is concentrated under reduced pressure
- customrecrystallized from ethyl acetate-n-hexane (2:1 by volume)
Sources & evidence
- ORD record
- ord-df35b6028ee04179be4a8269b53095d9
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04217130
Reaction notes
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