Hydrochloric Acid → HCID 66648155, compound

HRID 1983987Notes

Reaction equation

HRID 1983987 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[S:11](Cl)(=[O:13])=O)#[N:2].[CH3:15][NH2:16].[OH2:17].Cl.O1CCC[CH2:20]1>>[CH3:15][N:16]([CH3:20])[S:11]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[C:1]#[N:2])(=[O:13])=[O:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 55280391HCID 55280391, compound

Product 1

HCID 66648155HCID 66648155, compound

Procedure

A solution of 1.25 g (5.4 mmol) of 2-cyano-3-methoxyphenylsulfonyl chloride in 30 ml of tetrahydrofuran was added to a solution of 960 mg (12 mmol) of an aqueous solution of methylamine (40% by weight) in 20 ml of tetrahydrofuran at room temperature. The reaction mixture was stirred at room temperature for 30 minutes before water was added. The aqueous phase was acidified to pH=3 using hydrochloric acid (10% strength by weight, aqueous solution). The aqueous phase was then extracted three times with dichloromethane. The combined organic extracts were dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the resulting residue was triturated with methyl tert.-butyl ether. Yield: 0.28 g (23% of theory) of the title compound having a melting point of 121-128° C.

Workup

  1. additionwas added
  2. extractionThe aqueous phase was then extracted three times with dichloromethane
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue was triturated with methyl tert.-butyl ether

Sources & evidence

ORD record
ord-4d52595cdd2247c3a9cf8dc51f8fc5b5
Source dataset
uspto-grants-2009_06
Patent number
US07544637B2

Reaction notes

Loading…