Sodium Hydroxide → HCID 42630234, compound

HRID 1696760Notes

Reaction equation

HRID 1696760 reaction equation
[O-:1][C:2]#[N:3].[Na+].[C:5]1([CH3:15])[CH:10]=[CH:9][CH:8]=[C:7]([S:11](Cl)(=[O:13])=[O:12])[CH:6]=1.ClC1C=C(S(Cl)(=O)=O)C=CC=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[N:29]=1.[OH-].[Na+]>C(#N)C.C(OCC)(=O)C.N1C=CC=CC=1>[Cl:34][C:30]1[N:29]=[C:28]([NH:27][C:2]([NH:3][S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH3:15])[CH:6]=2)(=[O:13])=[O:12])=[O:1])[CH:33]=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 179093-Chlorobenzenesulphonyl chlorideHCID 2062462-Amino-6-chloropyridineHCID 517096Sodium CyanateHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 42630234HCID 42630234, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.128 g sodium cyanate in 3.0 ml acetonitrile was added 0.11 ml pyridine and 0.19 ml m-toluenesulfonyl chloride and the mixture was sonicated in a ultrasound bath at ca 40° C. for 1.5 h. HPLC showed disappearance of 3-Chloro-benzenesulfonyl chloride. The resulting suspension was added with stirring to a solution of 0.169 g 2-amino-6-chloropyridine in 1.0 ml of acetonitrile and the mixture was stirred at room temperature for 2 h. The reaction mixture was partioned between 0.1N sodium hydroxide and ethyl acetate (pH 10). The phases were separated and the aqueous phase was washed twice with ethyl acetate. The aqueous phase was acidified by addition of 25% hydrochloric acid and extracted with ethyl acetate, the organic phase was evaporated under reduced pressure. The residue was purified by silica column chromatography and crystallisation to yield 0.0995 g of a off-white solid. MS (ISN) M−H+=324.4

Workup

  1. customthe mixture was sonicated in a ultrasound bath at ca 40° C. for 1.5 h
  2. additionThe resulting suspension was added
  3. customThe phases were separated
  4. washthe aqueous phase was washed twice with ethyl acetate
  5. additionThe aqueous phase was acidified by addition of 25% hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customthe organic phase was evaporated under reduced pressure
  8. customThe residue was purified by silica column chromatography and crystallisation

Sources & evidence

ORD record
ord-a8ed77346ded44dd92ea905029a98e6c
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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