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

HRID 434532

Reaction equation

HRID 434532 reaction equation
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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3d90c9219f2f45b4aa0828f0ebcd286d
Source dataset
uspto-grants-1983_08
Patent number
US04397862

Linked notes

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