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

HRID 434532

반응식

HRID 434532 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d90c9219f2f45b4aa0828f0ebcd286d
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04397862

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