5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → HCID 10182243, compound

HRID 1781976Notes

Reaction equation

HRID 1781976 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[Cl:16][C:17]1[CH:30]=[CH:29][C:20]2[S:21][C:22]([S:25](Cl)(=[O:27])=[O:26])=[C:23]([CH3:24])[C:19]=2[CH:18]=1>N1C=CC=CC=1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:25]([C:22]3[S:21][C:20]4[CH:29]=[CH:30][C:17]([Cl:16])=[CH:18][C:19]=4[C:23]=3[CH3:24])(=[O:27])=[O:26])[CH:3]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 10182243HCID 10182243, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 3.05 g (15 mMol) of 5-amino-3-(2-dimethylaminoethyl)-1H-indol in 100 ml of pyridine is added dropwise at ambient temperature a solution of 4.21 g (15 mMol) of 5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride in 20 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hours. It is then evaporated to dryness, slightly alkalinised with diluted ammonia and dissolved in ethyl acetate. The organic phase is washed with water and a saturated solution of sodium bicarbonate, it is separated and dried with anhydrous sodium sulphate. The organic solution is evaporated to dryness and the resulting solid is repeatedly washed with ethyl ether, to yield 5.5 g (82%) of N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide as a solid with m.p.=226-227° C.

Workup

  1. customIt is then evaporated to dryness
  2. dissolutiondissolved in ethyl acetate
  3. washThe organic phase is washed with water
  4. customa saturated solution of sodium bicarbonate, it is separated
  5. dry with materialdried with anhydrous sodium sulphate
  6. customThe organic solution is evaporated to dryness
  7. washthe resulting solid is repeatedly washed with ethyl ether

Sources & evidence

ORD record
ord-65c80db4378345879329b129a789998c
Source dataset
uspto-grants-2009_03
Patent number
US07498328B2

Reaction notes

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