Thionyl Chloride → Chloride

HRID 485741ノート

反応式

HRID 485741 の反応式
[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]

参加物

9

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a14680f731b4f569539a16a622d5776
出典データセット
uspto-grants-1985_08
特許番号
US04537967

反応ノート

読み込み中…