Water → 3-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluoride

HRID 1784397Notes

Reaction equation

HRID 1784397 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[F-:22].[K+].C(#N)C.O>C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([S:16]([F:22])(=[O:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 522689Potassium FluorideHCID 542865763-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride

Product 1

HCID 575924833-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluorideYield 96.4%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonyl chloride (23 g, 67 mmol), potassium fluoride (12 g, 200 mmol), 18-crown-6 (0.1 g), and acetonitrile (100 mL) was stirred overnight. Water (200 mL) and ethyl acetate (200 mL) were added and the organic layer was washed with brine (100 mL), dried (MgSO4), and evaporated to give the title compound D1 as a white solid (21 g). 1H NMR 3 (d6-DMSO) 3.2 (4H, m), 3.7 (4H, m), 7.6 (1H, m), and 8.0 (2H, m).

Workup

  1. washthe organic layer was washed with brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d21019d42db04134bf3db7424f83b87b
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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