1,1'-Carbonyldiimidazole → HCID 19851611, compound

HRID 2291622Notes

Reaction equation

HRID 2291622 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8](O)=[O:9])[S:5][C:4]2[S:11][CH:12]=[CH:13][C:3]1=2.[C:14](N1C=CN=C1)([N:16]1C=CN=[CH:17]1)=O>O1CCCC1>[CH3:14][N:16]([CH3:17])[C:8]([C:6]1[S:5][C:4]2[S:11][CH:12]=[CH:13][C:3]=2[C:2](=[O:1])[CH:7]=1)=[O:9]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19086322HCID 19086322, compound

Product 1

HCID 19851611HCID 19851611, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a stirred solution of 4-oxo-4H-thieno[2,3-b]thiopyran-6-carboxylic acid (10.7 g, 0.05 mol) in tetrahydrofuran (50 ml) was added carbonyldiimidazole (8.9 g, 0.055 mol). The mixture was stirred at ambient temperature for 3/4 hour. Anhydrous dimethylamine was bubbled into the thick suspension at 0° C. until an excess was present. The resulting solution was stirred at 0° C. for 3/4 hour and the solvent was removed in vacuo. The residual oil was diluted with H2O (50 ml) and the solid which separated was filtered and dried to give 7.14 g of product, m.p. 126.5°-128 of 97% purity by HPLC. The aqueous filtrate was concentrated in vacuo and the residual gum was chromatographed on silica gel (200 g) using 10% methanol in chloroform. An additional 3.15 g of impure product was recovered. Yield was about 80%.

Workup

  1. customAnhydrous dimethylamine was bubbled into the thick suspension at 0° C. until
  2. stirringThe resulting solution was stirred at 0° C. for 3/4 hour
  3. customthe solvent was removed in vacuo
  4. additionThe residual oil was diluted with H2O (50 ml)
  5. customthe solid which separated
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-05871eebe8294924bc8f8f5d156928dc
Source dataset
uspto-grants-1989_01
Patent number
US04797413

Reaction notes

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