Benzene → Carboxymethyl Benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-thiocarboxylate

HRID 434532

反応式

HRID 434532 の反応式
C([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=O)[C:12]2=[CH:11][CH:10]=1)(=O)C1C=CC=CC=1.[S:20](Cl)(Cl)=O.CN(C)[CH:26]=[O:27].[C:29]([OH:33])(=[O:32])[CH2:30]S.[CH:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C.C(N(CC)CC)C.CCOCC>[C:26]([C:16]1([C:17](=[S:20])[O:19][CH2:30][C:29]([OH:33])=[O:32])[CH2:15][CH2:14][N:13]2[CH:9]=[CH:10][CH:11]=[C:12]12)(=[O:27])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

9

反応物 5

HCID 241BenzeneHCID 1133Thioglycolic AcidHCID 3826KetorolacHCID 6228DimethylformamideHCID 24386Thionyl Chloride

生成物 1

HCID 53956230Carboxymethyl Benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-thiocarboxylate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 1.0 g of 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid in 30 ml of dry benzene was added 0.29 ml of thionyl chloride and 0.03 ml of dimethylformamide. The mixture was left for 18 hours at room temperature and then evaporated under vacuum. To the residue so obtained were added 30 ml of ether, 1 ml of thioglycolic acid, and 1 ml of triethylamine. After 24 hours at room temperature, the reaction mixture was added to ethyl acetate, and the resultant solutions was washed with water, dried and evaporated. The residue so obtained was chromatographed on silica gel, eluting with 100:100:2 hexane:ethyl acetate:acetic acid, so as to obtain the desired product as a gum. This material was dissolved in 25 ml of ethyl acetate, and to the resulting solution was added a solution of 1.5 molar equivalents of sodium 2-ethylhexanoate in 20 ml of ethyl acetate. The sodium salt of the desired product precipitated out and was filtered, washed with ethyl acetate and dried under vacuum. The product has a decomposition point of 170°-180° C.

後処理

  1. customevaporated under vacuum
  2. customTo the residue so obtained
  3. waitAfter 24 hours at room temperature
  4. washthe resultant solutions was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue so obtained
  8. customwas chromatographed on silica gel
  9. washeluting with 100:100:2 hexane

出典と根拠

ORDレコード
ord-3d90c9219f2f45b4aa0828f0ebcd286d
出典データセット
uspto-grants-1983_08
特許番号
US04397862

関連ノート

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