Methanol → 8-Quinolinesulfonamide,n-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-

HRID 1164405Notes

Reaction equation

HRID 1164405 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([NH:12][C:13]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[CH:24]3)(=[O:18])=[O:17])=[O:14])[N:6]=1.[CH3:29][OH:30]>>[CH3:1][O:2][C:5]1[CH:10]=[C:9]([O:30][CH3:29])[N:8]=[C:7]([NH:12][C:13]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[CH:24]3)(=[O:18])=[O:17])=[O:14])[N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 130721688-Quinolinesulfonamide,n-[[(4,6-dichloro-2-pyrimidinyl)amino]carbonyl]-

Product 1

HCID 130721648-Quinolinesulfonamide,n-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-

Procedure

To 0.86 g sodium methoxide in 15 ml methanol is added 1.6 g of N-[(4,6-dichloropyrimidin-2-yl)aminocarbonyl]-8-quinolinesulfonamide portionwise. This mixture is then heated to reflux temperature for 2 hours. The resultant white suspension is cooled to room temperature and filtered. The filtered white solid is dissolved up in a minimum amount of water and carefully acidified with 10% aqueous hydrochloric acid. The resultant white solid is filtered to give 0.65 g, m.p. 175°-177° C.

Workup

  1. temperatureThis mixture is then heated
  2. temperatureto reflux temperature for 2 hours
  3. filtrationfiltered
  4. dissolutionThe filtered white solid is dissolved up in a minimum amount of water
  5. filtrationThe resultant white solid is filtered
  6. customto give 0.65 g, m.p. 175°-177° C.

Sources & evidence

ORD record
ord-dd34302b4d1a4860b57af81d33c767dc
Source dataset
uspto-grants-1983_01
Patent number
US04369320

Reaction notes

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