1,1'-Carbonyldiimidazole → HCID 69236439, compound

HRID 1593629Notes

Reaction equation

HRID 1593629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:15]([OH:17])=O)[CH2:6][C:5]2=1.C1N=C[N:20](C(N2C=NC=C2)=O)C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:15]([NH2:20])=[O:17])[CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21548699HCID 21548699, compound

Product 1

HCID 69236439HCID 69236439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (7c, 5.67 g, 22.71 mmole) dissolved THF (70 ml). N,N-carbonyldiimidazole (5.52 g, 44.81 mmole) was added. The reaction was stirred at ambient temperature for 3 hours. Ammonia was bubbled in for 1½ hours. The solid was filtered and discarded. Ethyl acetate (50 ml) was added to the filtrate and washed with citric acid 2 times, then the ethyl acetate phase was washed with 5% sodium bicarbonate and brine. The organic phase was concentrated in vacuo. The product was crystallized from the solution and filtered yielding a white solid, 4.39 g, 78%; mp. 247-248° C.

Workup

  1. customAmmonia was bubbled in for 1½ hours
  2. filtrationThe solid was filtered
  3. additionEthyl acetate (50 ml) was added to the filtrate
  4. washwashed with citric acid 2 times
  5. washthe ethyl acetate phase was washed with 5% sodium bicarbonate and brine
  6. concentrationThe organic phase was concentrated in vacuo
  7. customThe product was crystallized from the solution
  8. filtrationfiltered
  9. customyielding a white solid, 4.39 g, 78%

Sources & evidence

ORD record
ord-6096b17479354ad28150469d2348e6d5
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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