Trifluoroacetic acid → HCID 20450402, compound

HRID 358106Notes

Reaction equation

HRID 358106 reaction equation
COC1C=CC(C[O:10][C:11]([CH2:13][C:14]([O:16][C:17]2[CH:18]=[C:19]([C:23]3[N:24]=[C:25]4[N:29]([CH:30]=3)[C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[S:26]4)[CH:20]=[CH:21][CH:22]=2)=[O:15])=[O:12])=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(O)C.[ClH:53]>ClCCl.O1CCCC1>[ClH:53].[C:11]([CH2:13][C:14]([O:16][C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]3[N:29]([CH:30]=2)[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[S:26]3)[CH:20]=[CH:21][CH:22]=1)=[O:15])([OH:12])=[O:10]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13206728HCID 13206728, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 20450402HCID 20450402, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of anhydrous dichloromethane was dissolved 1.146 g of 2-[m-(p-methoxyphenylmethoxycarbonylacetoxy)phenyl]imidazo[2,1-b]benzothiazole and after adding thereto 0.4 ml of anisole, the mixture was cooled with ice-water. Then, 5 ml of trifluoroacetic acid was added dropwise to the mixture and the resultant mixture was stirred for one hour. The reaction mixture thus formed was concentrated under reduced pressure and the oily product thus obtained was dissolved in 10 ml of anhydrous tetrahydrofuran. Then, while stirring the mixture under ice-cooling, 2 ml of 2N hydrogen chloride ethanol solution was added to the solution and white crystals thus precipitated were recovered by filtration to provide 911 mg of 2-(m-carboxyacetoxyphenyl)imidazo[2,1-b]benzothiazole hydrochloride.

Workup

  1. additionafter adding
  2. customThe reaction mixture thus formed
  3. concentrationwas concentrated under reduced pressure
  4. customthe oily product thus obtained
  5. temperaturecooling
  6. customthus precipitated
  7. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-a6d31499b13c4a099b7626e686fd8ee8
Source dataset
uspto-grants-1984_08
Patent number
US04464384

Reaction notes

Loading…