Taurine → HCID 18981255, compound

HRID 1441139Notes

Reaction equation

HRID 1441139 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:19][CH2:20][CH2:21][S:22]([OH:25])(=[O:24])=[O:23]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:19][CH2:20][CH2:21][S:22]([OH:25])(=[O:24])=[O:23])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 1123TaurineHCID 773782,4,6-TrichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 18981255HCID 18981255, compoundYield 254.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2,4,6-trichloropyrimidine (6.9 g) in 75 ml of tetrahydrofuran is treated with diisopropylethylamine (15 ml) and solid taurine (4.7 g). The resulting suspension is heated at reflux for 48 hours. The reaction mixture is cooled to 20°-25° followed by solvent evaporation which gives 26 g of an oil which is chromatographed on 170 g of silica gel and eluting with chloroform/5.0M ammonia in methanol (7/3). An initial fraction of 250 mL is collected followed by 20 ml fractions. Fractions 23-57 contained the desired product. Solvent evaporation gives a semi-solid which is taken up in chloroform/methanol (10/1) and stirred at 20°-25° for 30 minutes. Filtration provided 3.71 g of a solid.

Workup

  1. temperatureThe resulting suspension is heated
  2. temperatureat reflux for 48 hours
  3. temperatureThe reaction mixture is cooled to 20°-25°
  4. customfollowed by solvent evaporation which

Sources & evidence

ORD record
ord-582b71ebc38746a484109ea42d5d31cc
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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