2,3-Dimercaptopropane → HCID 21462906, compound

HRID 1940504Notes

Reaction equation

HRID 1940504 reaction equation
[NH2:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH:20](OCC)OCC)[CH:14]=2)[C:3]1=[O:27].[CH2:28]([SH:32])[CH:29]([SH:31])[CH3:30]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[NH2:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH:20]3[S:31][CH:29]([CH3:30])[CH2:28][S:32]3)[CH:14]=2)[C:3]1=[O:27]

Participants

5

Reactant 2

HCID 612172,3-DimercaptopropaneHCID 21462900HCID 21462900, compound

Product 1

HCID 21462906HCID 21462906, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2.5 g (6.1 mmol) of 1-amino-3-(4-chloro-3-diethoxymethyl-phenyl)-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine, 2.0 g (18 mmol) of 1,2-propanedithiol and 50 mg of p-toluenesulfonic acid were refluxed in 100 mi of anhydrous toluene for six hours. After cooling, the mixture was washed with 10% strength sodium hydrogen carbonate solution and water, dried over sodium sulfate, concentrated and dried for 48 hours at reduced pressure. 2.1 g (80%) of a colorless oil were thus obtained, which is a 1:1 mixture of the two diastereomers.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with 10% strength sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customdried for 48 hours at reduced pressure

Sources & evidence

ORD record
ord-689e4998c1a54c39affa1e24614711b1
Source dataset
uspto-grants-1997_12
Patent number
US05700805

Reaction notes

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