Acetic Acid → HCID 86755524, compound

HRID 2288581Notes

Reaction equation

HRID 2288581 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH3:9][N+:10]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](=[S:36])[O:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2.C(O)(=O)C>C(Cl)Cl.C(O)(C)C.[Zn]>[CH3:9][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]([C:24](=[S:36])[O:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]1=2

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 18006796HCID 18006796, compound

Product 1

HCID 86755524HCID 86755524, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Naphthyl 10-methylacridinium-9-thiocarboxylate triflate (65.50 g) was suspended in CH2Cl2 (1000 mL) under argon and glacial acetic acid (21.2 ml) and zinc (40.43 g) were added. After stirring overnight, TLC showed the dissappearance of the starting material and the formation of a new product. The reaction mixture was filtered through a bed of silica gel and the CH2Cl2 removed in vacuo. The slightly yellow solid obtained was stirred in isopropanol (500 ml), filtered, washed with 500 ml more isopropanol, and allowed to air dry. The pure product (46.36 g) was thereby obtained. 1H NMR (CDCl3) δ 3.47 (s, 3H) , 5.13 (s, 1H) , 7.00-7.06 (m, 4H) , 7.25-7.49 (m, 7H) , 7.70-7.79 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of silica gel
  2. customthe CH2Cl2 removed in vacuo
  3. customThe slightly yellow solid obtained
  4. filtrationfiltered
  5. washwashed with 500 ml more isopropanol
  6. customto air dry

Sources & evidence

ORD record
ord-01a5afd823094fd198ea7969a8fc2e15
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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