Chlorosulfonic acid → 3-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride

HRID 1784396Notes

Reaction equation

HRID 1784396 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Cl:18][S:19](O)(=[O:21])=[O:20]>ClCCl>[F:17][C:2]([F:1])([F:16])[C:3]([N:5]1[CH2:6][CH2:7][C:8]2[CH:15]=[CH:14][C:13]([S:19]([Cl:18])(=[O:21])=[O:20])=[CH:12][C:9]=2[CH2:10][CH2:11]1)=[O:4]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 542865763-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chlorideYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine (see WO02/40471) (20 g, 80 mmol) in dichloromethane (50 mL) was added dropwise to a solution of chlorosulfonic acid (33 mL, 240 mmol) in more dichloromethane (200 mL) at 0° C. The resulting solution was stirred for 18 h without cooling then poured onto ice (250 g). The resulting organic layer was washed with brine (100 mL), dried (MgSO4), and evaporated to give the subtitle compound as a white solid (23 g).

Workup

  1. temperaturewithout cooling
  2. additionthen poured onto ice (250 g)
  3. washThe resulting organic layer was washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7c3d95e326b64e739752398e1f3b3878
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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