1,1'-Carbonyldiimidazole → HCID 178458739, compound

HRID 128708Notes

Reaction equation

HRID 128708 reaction equation
[CH:1]([O:4][C:5]1[C:9]2[CH2:10][S:11](=[O:14])[CH2:12][CH2:13][C:8]=2[S:7][C:6]=1[C:15]([OH:17])=O)([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:30][C:31]1[NH:35][N:34]=[N:33][N:32]=1>CN(C=O)C>[NH:32]1[C:31]([NH:30][C:15]([C:6]2[S:7][C:8]3[CH2:13][CH2:12][S:11](=[O:14])[CH2:10][C:9]=3[C:5]=2[O:4][CH:1]([CH3:3])[CH3:2])=[O:17])=[N:35][N:34]=[N:33]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 19374944HCID 19374944, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178458739HCID 178458739, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 0.494 g (1.8 mM) of 3-isopropoxy-5-oxo-6,7-dihydro-4H-thieno[3,2-c]thiopyran-2-carboxylic acid (from Preparation 13) in 10 mL of DMF were added 0.438 g (2.7 mmol) of 1,1'-carbonyldiimidazole. The reaction mixture was heated at 80° C. for 60 minutes, followed by addition in one portion of 0.283 g (3.33 mmol) of 5-aminotetrazole. The reaction mixture was heated at 80° C. for 5 hours, cooled to 24° C., and stirred for an additional 18 hours. The mixture was concentrated to dryness by evaporation of the solvent under reduced pressure. The residue was dissolved in 100 mL of chloroform, washed with 2N HCl, water, brine, dried over MgSO4, and the solvent was removed by evaporation under reduced pressure. The solid residue was recrystallized from methanol/diethyl ether to afford 0.279 g of 3-isopropoxy-5-oxo-6,7-dihydro-4H-thieno[3,2-c] thiopyran-2-carboxylic acid (1H-tetrazol-5-yl) amide, mp 225°-226° C.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 5 hours
  2. temperaturecooled to 24° C.
  3. concentrationThe mixture was concentrated to dryness by evaporation of the solvent under reduced pressure
  4. dissolutionThe residue was dissolved in 100 mL of chloroform
  5. washwashed with 2N HCl, water, brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customThe solid residue was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-af251a4151ef497fa79d1ed1ea3ace13
Source dataset
uspto-grants-1995_11
Patent number
US05464855

Reaction notes

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