Thionyl Chloride → Chloride

HRID 485741노트

반응식

HRID 485741 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=[O:13])[NH:3]1.[C:15]([CH2:18][CH2:19][C:20]([Cl:22])=[S:21])(=[O:17])[CH3:16].S(Cl)(Cl)=O.C(CCC(O)=S)(=O)C>C(#N)C.C1C=CC=CC=1.C(N(CC)CC)C>[Cl-:22].[C:15]([CH2:18][CH2:19][C:20]([N:3]1[CH:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1])=[S:21])(=[O:17])[CH3:16]

참가 물질

9

반응물 4

HCID 24386Thionyl ChlorideHCID 48361591-Oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 200413153-Acetylthiopropionyl chlorideHCID 178467872HCID 178467872, 화합물

생성물 2

HCID 312ChlorideHCID 202695542-(3-Acetylthiopropionyl)-1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid

시약·촉매·용매 3

HCID 241Benzene용매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

1.1 g of triethyl amine was added to a suspension of 1.0 g of 1-oxo-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid in 10 ml of acetonitrile. A solution of 3-acetylthiopropionyl chloride (3-acethylthiopropionyl chloride was prepared by adding 1.0 g of thionyl chloride to a solution of 0.8 g of 3-acetylthiopropionic acid in 5 ml of benzene, stirring the solution overnight at room temperature and distilling off the solvent and excess thionyl chloride) in 5 ml of acetonitrile was added drop by drop to the suspension which was ice-cooled. After stirring the mixture for 2 hours at room temperature, the solvent was distilled off, 20 ml of ethylacetate and 10 ml of water were added to the residue and the solution was shaken and the organic phase separated and washed. The organic phase was dried over anhydrous Glauber's salt, the solvent was distilled off and then the residue was recrystalized from benzene to obtain 0.9 g of 2-(3-acetylthiopropionyl)-1-oxo-1,2,3,4-tetrahydro- 3-isoquinoline carboxylic acid as a colorless microcrystalline material.

후처리

  1. distillationdistilling off the solvent and excess thionyl chloride) in 5 ml of acetonitrile
  2. additionwas added drop by drop to the suspension which
  3. temperaturecooled
  4. stirringAfter stirring the mixture for 2 hours at room temperature
  5. distillationthe solvent was distilled off
  6. addition20 ml of ethylacetate and 10 ml of water were added to the residue
  7. stirringthe solution was shaken
  8. customthe organic phase separated
  9. washwashed
  10. dry with materialThe organic phase was dried over anhydrous Glauber's salt
  11. distillationthe solvent was distilled off
  12. customthe residue was recrystalized from benzene

출처 및 근거

ORD 기록
ord-6a14680f731b4f569539a16a622d5776
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04537967

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