2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 68195093, compound

HRID 2370641Notes

Reaction equation

HRID 2370641 reaction equation
ClC(Cl)(Cl)S(O[CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[CH3:14][C:15]1([CH3:28])[C:24]2[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=2)[CH2:18][NH:17][CH2:16]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:14][C:15]1([CH3:28])[C:24]2[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=2)[CH2:18][N:17]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH2:16]1

Participants

5

Reactant 3

HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 516892Sodium BicarbonateHCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 68195093HCID 68195093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2,2,2-Trifluoroethyl trichloromethanesulfonate (1.8 g, 6.40 mmol) was added to a solution of 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.8 g, 3.88 mmol) and sodium bicarbonate (0.66 g, 7.86 mmol) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred at 60° C. for 16 hour. The mixture was concentrated, and CH2Cl2 (70 mL) and water (70 mL) were added to the residue. After separation, the aqueous layer was extracted with CH2Cl2 again. The combined organic layers were washed with saturated aqueous NaCl (1×150 mL), dried over Na2SO4, filtered, and concentrated to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionCH2Cl2 (70 mL) and water (70 mL) were added to the residue
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with CH2Cl2 again
  5. washThe combined organic layers were washed with saturated aqueous NaCl (1×150 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b7b2fb5d72794d55a8a79d5ab467f5f5
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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