4-Cyanobenzenesulfonyl chloride → HCID 21221824, compound

HRID 1585169Notes

Reaction equation

HRID 1585169 reaction equation
[CH2:1]([N:4]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:19][NH2:20])=[C:13]([CH2:17][NH2:18])[CH:14]=2)[CH2:9]1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)#[N:22]>N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([N:4]([CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH2:17][NH:18][S:29]([C:26]3[CH:25]=[CH:24][C:23]([C:21]#[N:22])=[CH:28][CH:27]=3)(=[O:31])=[O:30])=[C:12]([CH2:19][NH:20][S:29]([C:26]3[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[CH:11]=2)[CH2:16]1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 21221809HCID 21221809, compound

Product 1

HCID 21221824HCID 21221824, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 2-(N,N-dipropylamino)-5,6-bis(aminomethyl)indane 52 (0.276 g, 1.00 mmol) in pyridine (4.0 ml) was cooled in ice, and 4-cyanobenzenesulfonyl chloride (0.61 g, 3.0 mmol) was added. The mixture was stirred at room temperature for 4 hours. The mixture was diluted with 10% sodium carbonate solution and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a dark oil. Purification by flash chromatography (230-400 mesh silica gel, 60-80% ethyl acetate/hexane) gave the title compound (54) as an oil. The compound was dissolved in ethyl acetate and excess ethereal hydrochloric acid was added. The mixture was diluted with diethylether and filtered. The precipitate was washed with diethylether and dried under vacuum giving the hydrochloride salt of 54 as a tan solid (0.143 g).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under vacuum
  5. customto leave a dark oil
  6. customPurification by flash chromatography (230-400 mesh silica gel, 60-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-64d01416f027417290e3442bfd9f2071
Source dataset
uspto-grants-1999_08
Patent number
US05936000

Reaction notes

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