3,5-Dichlorobenzenesulfonyl chloride → HCID 59334863, compound

HRID 1510315Notes

Reaction equation

HRID 1510315 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]2.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[C:23]([Cl:25])[CH:24]=1>N1C=CC=CC=1.ClCCl>[Cl:25][C:23]1[CH:22]=[C:21]([S:26]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]3)(=[O:27])=[O:28])[CH:20]=[C:19]([Cl:18])[CH:24]=1

Participants

5

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 22240520tert-Butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 59334863HCID 59334863, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

6 g tert-butyl 5-amino-2,3-dihydro-indole-1-carboxylate are dissolved in 50 ml of pyridine and 50 ml dichloromethane. To this is added dropwise a solution of 6.5 g 3,5-dichlorophenylsulphonyl chloride in 50 ml dichloromethane and the mixture is stirred for 1 hour at ambient temperature. Then it is diluted with dichloromethane and washed with 1 N hydrochloric acid and with saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 30:70).

Workup

  1. washwashed with 1 N hydrochloric acid and with saturated sodium chloride solution
  2. dry with materialAfter drying with magnesium sulphate the solvents
  3. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 30:70)

Sources & evidence

ORD record
ord-39ad76e7566a4fa5ba8fa6a002638145
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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