Pyridine → HCID 86611312, compound

HRID 1431975Notes

Reaction equation

HRID 1431975 reaction equation
[CH2:1](N)[C:2]#[CH:3].[N:5]1C=CC=CC=1.[Cl:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:3]([C:13]1[C:12]([Cl:11])=[CH:17][CH:16]=[CH:15][C:14]=1[S:18]([NH2:5])(=[O:20])=[O:19])[C:2]#[CH:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 239041Propargylamine

Product 1

HCID 86611312HCID 86611312, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

To a stirred solution of propargylamine (0.78 ml, 12.0 mmol) and pyridine (3.0 ml) in CH2Cl2 (30 ml), 4-dimethylaminopyridine (122 mg, 1.0 mmol) and a solution of m-chlorobenzenesulfonyl chloride (2.11 g, 10.0 mmol) in CH2Cl2 are added at 4° C. The reaction mixture is stirred for 30 min at 4° C. and for 12 h at room temperature. The reaction mixture is extracted with CH2Cl2 and aqueous 1 N HCl solution, the organic layer dried over MgSO4, the solvents evaporated and the solid residue suspended in a mixture of hexane/ethyl acetate (1:8), filtered and dried under reduced pressure to yield the title compound as beige solid. 1H-NMR (300 MHz, CDCl3): 7.95-7.9; 7.9-7.75; 7.65-45 (3m, 4H); 4.85 (br.s, 1H); 3.95-3.9 (m, 2H); 2.14 (t, J=2.5 Hz, 1H).

Workup

  1. extractionThe reaction mixture is extracted with CH2Cl2 and aqueous 1 N HCl solution
  2. dry with materialthe organic layer dried over MgSO4
  3. customthe solvents evaporated
  4. additionthe solid residue suspended in a mixture of hexane/ethyl acetate (1:8)
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a9991ef2b5624a63a6ee6d1d44dd2b02
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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