4-Toluenesulfonyl chloride → HCID 131723208, compound

HRID 1934341Notes

Reaction equation

HRID 1934341 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]3[CH:29]=[C:30]([O:36][CH2:37][CH3:38])[C:31]([O:33][CH2:34][CH3:35])=[CH:32][C:27]=3[C@H:26]3[C@H:21]([CH2:22][CH2:23][N:24]([CH3:39])[CH2:25]3)[N:20]=2)=[CH:15][CH:14]=1>ClCCl.N1C=CC=CC=1>[CH2:37]([O:36][C:30]1[C:31]([O:33][CH2:34][CH3:35])=[CH:32][C:27]2[C@H:26]3[C@H:21]([CH2:22][CH2:23][N:24]([CH3:39])[CH2:25]3)[N:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([NH:12][S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=4)(=[O:9])=[O:8])=[CH:14][CH:15]=3)[C:28]=2[CH:29]=1)[CH3:38]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 131723209HCID 131723209, compound

Product 1

HCID 131723208HCID 131723208, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.3 g p-toluenesulfonic acid chloride in 5 ml absolute dichloromethane is added dropwise to a solution of 3.5 g (−)-cis-6-(4-Aminophenyl)-8,9-diethoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo-[c][1,6]naphthyridine in 20 ml absolute pyridine, and the mixture is then stirred at room temperature for a further 3 h. After the evaporation of the solvents, the residue is extracted with dilute sodium hydroxide solution and dichloromethane. The organic phase is then washed with water, dried over sodium sulfate and concentrated. 5.4 g of the title compound are obtained as rough product, which is recrystallised twice in ethyl acetate/methanol. Yield: 4.3 g yellowish crystalls. M.p. 267-268° C.

Workup

  1. customAfter the evaporation of the solvents
  2. extractionthe residue is extracted with dilute sodium hydroxide solution and dichloromethane
  3. washThe organic phase is then washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e2af550f6794b428b150fa54c12e994
Source dataset
uspto-grants-2002_05
Patent number
US06384047B1

Reaction notes

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