Sodium Hydroxide → HCID 13533293, compound

HRID 463621Notes

Reaction equation

HRID 463621 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[Cl:11][C:12]1[C:17]([S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>C(#N)C.O>[Cl:11][C:12]1[C:17]([S:18]([NH:21][C:22]([NH:1][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=2)=[O:23])(=[O:19])=[O:20])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 130384352-Chloro-3-pyridinesulfonylisocyanate

Product 1

HCID 13533293HCID 13533293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 20 ml of dry acetonitrile at room temperature was added 2.2 g of 2-chloropyridine-3-sulfonylisocyanate. The mixture was stirred for several hours and filtered. Evaporation of the filtrate yielded a solid residue which was stirred in approximately 30 ml of water while adjusting the pH of this mixture to 11 by the addition of 10% of NaOH. This solution was filtered, the filtrate pH adjusted to pH 7 by adding 10% hydrochloric acid and the resulting neutral solution was again filtered. The desired product was then precipitated from this filtrate by adjusting the pH to 2, collected in a sintered funnel and dried in a vacuum oven at room temperature. It melted at 165°-168°.

Workup

  1. filtrationfiltered
  2. customEvaporation of the filtrate
  3. customyielded a solid residue which
  4. filtrationThis solution was filtered
  5. additionby adding 10% hydrochloric acid
  6. filtrationthe resulting neutral solution was again filtered
  7. customThe desired product was then precipitated from this filtrate
  8. customcollected in a sintered funnel
  9. customdried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-5ea26f23813742a2a2485ae903d14b52
Source dataset
uspto-grants-1985_10
Patent number
US04544401

Reaction notes

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