Benzoyl chloride → HCID 9885305, compound

HRID 1742931Notes

Reaction equation

HRID 1742931 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]([O:18]CC)=[O:17])=[N:15][N:6]3[C:5](=[O:21])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:29]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[N:15][N:6]3[C:5](=[O:21])[C:4]=2[CH:3]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86748093HCID 86748093, compound

Product 1

HCID 9885305HCID 9885305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-amino-4,9-dihydro-4-methyl-9-oxopyrazolo[5,1-b]quinazoline-2-carboxylic acid, ethyl ester (0.75 g, 2.62 mmol, Example 2) and triethylamine (0.46 mL, 3.30 mmol) in 500 mL of methylene chloride was added dropwise a solution of benzoyl chloride (0.34 mL, 2.93 mmol) in 50 mL of methylene chloride at room temperature. A yellow solid slowly formed. The mixture was stirred at room temperature for 12 hours and filtered. The yellow solid was washed with methylene chloride and diethyl ether and vacuum-dried, affording the title compound as its ethyl ester, mp 275°-278° C., dec.

Workup

  1. customA yellow solid slowly formed
  2. filtrationfiltered
  3. washThe yellow solid was washed with methylene chloride and diethyl ether
  4. customvacuum-dried

Sources & evidence

ORD record
ord-79e97923400147518e7b5c93a8fcda28
Source dataset
uspto-grants-1994_08
Patent number
US05342942

Reaction notes

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