Trifluoromethanesulfonic acid → HCID 86613110, compound

HRID 645390Notes

Reaction equation

HRID 645390 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:20]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>ClC(Cl)C.C(OCC)(=O)C>[F:19][C:2]([F:18])([F:1])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([Br:20])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 67184N-bromobutanimideHCID 86613107HCID 86613107, compound

Product 1

HCID 86613110HCID 86613110, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of (S)-N-Trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.875 g, 3.0 mmol) in dichloroethane (7 mL) was treated with N-bromosuccinimide (0.284 g, 2.1 mmol) and trifluoromethansulfonic acid (0.639 g, 4.2 mmol). The reaction was stirred for 16 h at 75° C., diluted with ethyl acetate (20 mL) and extracted with water (2×10 mL). The organics were dried with MgSO4, filtered and concentrated. Flash chromatography (5% EtOAc in hexanes, silica) resulted in 0.13 g of a clear oil. MS calculated for C13H12BrClF3NO+H: 370, observed: 370.

Workup

  1. extractionextracted with water (2×10 mL)
  2. dry with materialThe organics were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-607138cf2b8e428b9b1bafd8cf22bf03
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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