Thionyl Chloride → HCID 56629765, compound

HRID 127578

Reaction equation

HRID 127578 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1.[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(SCC(C)C(O)=O)(=O)C1C=CC=CC=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:16]([S:24][CH2:25][CH:26]([CH3:30])[C:27]([N:3]1[C@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 5694973-(Benzoylthio)-2-methylpropanoic acidHCID 2760578methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochlorideHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

Product 1

HCID 56629765HCID 56629765, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

5.69 g of methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride are suspended in 50 ml of chloroform, and 5.6 g of triethylamine are added thereto under ice-cooling and stirring. 3-benzoylthio-2-methylpropionyl chloride (which is prepared by heating a mixture of 5.6 g of 3-benzoylthio-2-methyl-propionic acid and 6 ml of thionyl chloride at 60° C. for 2 hours, followed by distillation thereof to remove the excess of thionyl chloride) is dissolved in 10 ml of tetrahydrofuran, and said tetrahydrofuran solution is added dropwise to the suspension obtained above. After the mixture is stirred at room temperature overnight, the chloroform layer is collected therefrom and washed with water, an aqueous sodium bicarbonate solution, diluted hydrochloric acid and water, successively. The chloroform solution is dried and then distilled to remove solvent. The residue thus obtained is purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1)). 8.0 g of methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate are obtained as colorless oil. Yield: 80.5 %

Workup

  1. temperatureunder ice-cooling
  2. temperatureby heating
  3. distillationfollowed by distillation
  4. customto remove the excess of thionyl chloride)
  5. dissolutionis dissolved in 10 ml of tetrahydrofuran
  6. additionis added dropwise to the suspension
  7. customobtained above
  8. stirringAfter the mixture is stirred at room temperature overnight
  9. customthe chloroform layer is collected
  10. washwashed with water
  11. dry with materialThe chloroform solution is dried
  12. distillationdistilled
  13. customto remove solvent
  14. customThe residue thus obtained
  15. customis purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1))

Sources & evidence

ORD record
ord-2813aaff273042e3820a4bb2b0273ddf
Source dataset
uspto-grants-1981_03
Patent number
US04256751

Linked notes

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