Methyl triflate → 10-Methyl-9-(phenoxycarbonyl)acridin-10-ium trifluoromethanesulfonate

HRID 2395922Notes

Reaction equation

HRID 2395922 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[F:24][C:25]([F:32])([F:31])[S:26]([O:29]C)(=[O:28])=[O:27]>C(Cl)Cl>[F:24][C:25]([F:32])([F:31])[S:26]([O-:29])(=[O:28])=[O:27].[CH3:25][N+:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13]([C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 517916Phenyl acridine-9-carboxylate

Product 1

HCID 1547628210-Methyl-9-(phenoxycarbonyl)acridin-10-ium trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl acridine-9-carboxylate (530 mg, 1.7 mmol) was dissolved in methylenechloride (5 mL) under argon and methyl trifluoromethanesulfonate (1 mL, 8.8mmol) was added. The solution was stirred overnight at room temperature to yield a thick yellow precipitate. This precipitate was filtered, washed with ether and dried to obtain the product as yellow crystals. 1H NMR (acetone-d6) δ5.22 (s, 3H), 7.47-7.71 (m, 5H), 8.23-9.07 (m, 8H).

Workup

  1. customto yield a thick yellow precipitate
  2. filtrationThis precipitate was filtered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-2325b06de1704d48b6a2caa2ac0107c9
Source dataset
uspto-grants-1996_02
Patent number
US05491072

Reaction notes

Loading…