1,1'-Carbonyldiimidazole → HCID 19898811, compound

HRID 1196490Notes

Reaction equation

HRID 1196490 reaction equation
[C:1]1([C:7]2[C:15]([CH2:16][C:17]([OH:19])=O)=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O>O1CCCC1>[C:1]1([C:7]2[C:15]([CH2:16][C:17]([NH2:22])=[O:19])=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19898801HCID 19898801, compound

Product 1

HCID 19898811HCID 19898811, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.5 g (0.013 mole) of 2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid and 2.24 g (0.013 mole) of 1,1'-carbonyldiimidazole in 150 ml of anhydrous tetrahydrofuran was stirred for 3 hours at room temperature while nitrogen was bubbled through the mixture. The reaction mixture was cooled in a dry ice/acetone bath, and treated with 50 ml of liquid ammonia. The reaction mixture was warmed to room temperature and stirred for two days. The suspended solid which formed was collected by filtration (2.81 g, mp 204°-219° C.) combined with the residue from evaporation of the filtrate (3.1 g), and recrystallized from ethanol to give 2.1 g of product (60%), mp 217°-219° C.

Workup

  1. customwas bubbled through the mixture
  2. temperatureThe reaction mixture was cooled in a dry ice/acetone bath
  3. additiontreated with 50 ml of liquid ammonia
  4. temperatureThe reaction mixture was warmed to room temperature
  5. stirringstirred for two days
  6. customThe suspended solid which formed
  7. filtrationwas collected by filtration (2.81 g, mp 204°-219° C.)
  8. customcombined with the residue from evaporation of the filtrate (3.1 g)
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9bd7a6359cda470289e18b24e99493a0
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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