2-Chlorobenzenesulfonyl chloride → HCID 44256011, compound

HRID 1444614Notes

Reaction equation

HRID 1444614 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].Cl.Cl.[CH2:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:30][CH2:29][C:28]2[C:31]3[CH:21]1[CH2:22][CH2:23][C:24]=3[C:25]([O:34][CH3:35])=[C:26]([O:32][CH3:33])[CH:27]=2)[CH3:15].CCN(C(C)C)C(C)C>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:16]([CH2:17][CH2:18][CH2:19][N:20]1[CH2:30][CH2:29][C:28]2[C:31]3[CH:21]1[CH2:22][CH2:23][C:24]=3[C:25]([O:34][CH3:35])=[C:26]([O:32][CH3:33])[CH:27]=2)[CH2:14][CH3:15])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67099322HCID 67099322, compound

Product 1

HCID 44256011HCID 44256011, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chlorobenzenesulfonyl chloride (246.1 mg, 1.17 mmol) was added to a solution of Ethyl-[3-(7,8-Dimethoxy-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-propyl]-amine dihydro-chloride (400 mg, 1.06 mmol) and N,N′-diisopropylethylamine (1.01 ml, 6.4 mmol) in CH2Cl2 (20 mL) and the mixture was stirred overnight at room temperature. The resulting solution was washed with water (3×20 mL), dried over Na2SO4 and evaporated to dryness. The free base was dissolved in ethyl acetate and A 2.8 M solution of hydrogen chloride in ethanol (0.50 mL) was then added. The product was crystallized and collected by filtration, and vacuum dried to give a white solid (233 mg, 43%).

Workup

  1. washThe resulting solution was washed with water (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe free base was dissolved in ethyl acetate
  5. additionA 2.8 M solution of hydrogen chloride in ethanol (0.50 mL) was then added
  6. customThe product was crystallized
  7. filtrationcollected by filtration, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-754355d3ddea4b738d733a6cfb15612e
Source dataset
uspto-grants-2010_02
Patent number
US07662862B2

Reaction notes

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