4-Toluenesulfonyl chloride → 3-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazoline

HRID 1581628Notes

Reaction equation

HRID 1581628 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[N:17][N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:28])[NH:20][C:19]=12.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C)C=O.O>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[N:17][N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([O:28][S:35]([C:32]3[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=3)(=[O:37])=[O:36])=[N:20][C:19]=12

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178518573HCID 178518573, compound

Product 1

HCID 865873523-(2-Fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-a]quinazolineYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (5.6 ml, 40 mmol) was added to a stirred solution of 3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5(4H)-one (5.47 g, 19.5 mmol) and p-toluenesulfonyl chloride (3.82 g, 20 mmol) in dry N,N-dimethylformamide (100 ml) at room temperature under nitrogen. The brown suspension was stirred for 18 h then diluted with water (800 ml). The yellow precipitate was collected, washed sequentially with water and diethyl ether, then dried in vacuo to give 3-(2-fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-α]quinazoline (8.65 g, 100%). δH (400 MHz; CDCl3) 2.42 (3H, s), 7.23 (2H, d, J=8), 7.28-7.34 (2H, m), 7.47-7.50 (1H, m), 7.76 (1H, dd, J=8 and 8), 7.87 (1H, ddd, J=7, 7 and 2), 8.04-8.08 (3H, m), 8.30 (1H, dd, J=8 and 1), 8.70 (1H, d, J=8); m/z (ES+) 435 (M+H+).

Workup

  1. customThe yellow precipitate was collected
  2. washwashed sequentially with water and diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bf36ace67f7e41c0b205a178747b4426
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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