Chlorosulfonic acid → 10-Trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-4-sulfonyl chloride

HRID 395313Notes

Reaction equation

HRID 395313 reaction equation
[CH:1]12[CH2:18][CH:8]([CH2:9][N:10]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:11]1)[C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=1.[Cl:19][S:20](O)(=[O:22])=[O:21]>>[F:14][C:13]([F:15])([F:16])[C:12]([N:10]1[CH2:11][CH:1]2[CH2:18][CH:8]([C:7]3[CH:6]=[CH:5][C:4]([S:20]([Cl:19])(=[O:22])=[O:21])=[CH:3][C:2]=32)[CH2:9]1)=[O:17]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 218647322,2,2-Trifluoro-1-(1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)ethan-1-one

Product 1

HCID 2186469110-Trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-4-sulfonyl chlorideYield 87%

Procedure

1-(10-Aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (530 mg, 2.1 mmol) was added to chlorosulfonic acid (2 mL, 30 mmol) and stirred for 5 minutes. The mixture was quenched with ice, extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated to provide an oil (640 mg, 87%). (TLC 30% ethyl acetate/hexanes Rf 0.15).

Workup

  1. customThe mixture was quenched with ice
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c38150a0feaf40349928abd9c5e08512
Source dataset
uspto-grants-2003_08
Patent number
US06605610B1

Reaction notes

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