Propionic Acid → N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl]propionamide

HRID 378639Notes

Reaction equation

HRID 378639 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([SH:9])=[C:4]([CH3:10])[CH:3]=1.[NH2:11][C:12]([CH3:16])([CH3:15])[CH2:13]O.[C:17](O)(=[O:20])[CH2:18][CH3:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9][CH2:13][C:12]([NH:11][C:17](=[O:20])[CH2:18][CH3:19])([CH3:16])[CH3:15])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 118072-Amino-2-methyl-1-propanolHCID 1088624-Chloro-2,5-dimethylbenzenethiol

Product 1

HCID 22007459N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl]propionamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2,5-dimethylbenzenethiol (17.25 g), 2-amino-2-methylpropanol (8.9 g), propionic acid (7.4 g) and toluene (50 ml) was reacted to give a solid which was recrystallised from petroleum ether, b.p. 60-80° C. to give N-[2-(4-chloro-2,5-xylylthio)-1,1-dimethylethyl] propionamide, m.p. 78-81° C. This product (15.0 g) and concentrated hydrochloric acid (18 ml) were boiled under reflux for 25 hours give an oil which was purified by flash column chromatography on silica using ethyl acetate and then ethyl acetate/methanol (4:1) as the mobile phase to give 2-(4-chloro-2,5-xylylthio)-1,1-dimethylethylamine as an oil.

Workup

  1. customwas reacted
  2. customto give a solid which
  3. customwas recrystallised from petroleum ether, b.p. 60-80° C.

Sources & evidence

ORD record
ord-4185544a36ce4ab1bff3c99726ced250
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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