Sulfuric Acid → HCID 178513810, compound

HRID 76373Notes

Reaction equation

HRID 76373 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[N:12]=[C:11]([C:13]#[N:14])[C:10]([OH:15])=[N:9][CH:8]=1.[OH-:16].[Na+]>O>[F:6][C:7]1[N:12]=[C:11]([C:13]([NH2:14])=[O:16])[C:10]([OH:15])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178510584HCID 178510584, compound

Product 1

HCID 178513810HCID 178513810, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

14.39 g of concentrated sulfuric acid was added to 3.45 g of the oily 6-fluoro-3-hydroxypyrazine-2-carbonitrile, and the resulting mixture was stirred at 50° C. for 4 hours. The reaction mixture was then added dropwise over a period of 20 minutes to 44.5 ml of water that had been cooled to 3° C. Following completion of the dropwise addition, the resulting mixture was stirred for 20 minutes at a temperature of not more than 10° C. Subsequently, 10.17 g of a 28% aqueous solution of sodium hydroxide was added dropwise to the reaction mixture over a period of 15 minutes. Following completion of the dropwise addition, the mixture was stirred at the same temperature for 30 minutes. The solid product was then filtered off, and washed with 18 ml of water, yielding 2.22 g (yield: 92.3%) of 6-fluoro-3-hydroxypyrazine-2-carboxamide.

Workup

  1. temperaturehad been cooled to 3° C
  2. additioncompletion of the dropwise addition
  3. stirringthe resulting mixture was stirred for 20 minutes at a temperature of not more than 10° C
  4. additioncompletion of the dropwise addition
  5. stirringthe mixture was stirred at the same temperature for 30 minutes
  6. filtrationThe solid product was then filtered off
  7. washwashed with 18 ml of water

Sources & evidence

ORD record
ord-0c2eb05f05ba43aab6ad0f97b9786b37
Source dataset
uspto-grants-2014_09
Patent number
US08835636B2

Reaction notes

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