Ammonium Sulfate → HCID 23446125, compound

HRID 1841442Notes

Reaction equation

HRID 1841442 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:9][C:10]1[N:11]=[C:12]([S:21][CH3:22])[N:13]=[N:14][C:15]=1[C:16](OCC)=[O:17])[CH3:8].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C1COCC1>[CH2:7]([NH:9][C:10]1[N:11]=[C:12]([S:21][CH3:22])[N:13]=[N:14][C:15]=1[CH2:16][OH:17])[CH3:8]

Participants

5

Reactant 3

HCID 6097028Ammonium Sulfate2×HCID 12098502HCID 12098502, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23446125HCID 23446125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a room temperature suspension of 5.1 g (133.7 mmol) of lithium aluminum hydride in 400 mL of anhydrous THF was added a solution of 16.2 g (66.9 mmol) of 5-ethylamino-3-methylsulfanyl-1,2,4-triazine-6-carboxylic acid, ethyl ester in 150 mL of THF. The reaction was stirred for 6 hours at room temperature, at which time approximately 16 mL of a saturated solution of ammonium sulfate was added dropwise while keeping the reaction temperature below 25° C. with an ice bath. The reaction mixture becomes heavy with precipitate, and 200 mL of THF was added followed by 5 mL more of saturated ammonium sulfate. The reaction mixture was stirred for another 30 minutes and decanted. The remaining solids were filtered and washed several times with a total of 1 L of hot THF. The combined THF solution was concentrated and twice dissolved in dichloromethane and concentrated to give a pale orange semi-solid, (5-ethylamino-3-methylsulfanyl-1,2,4-triazin-6-yl)-methanol.

Workup

  1. additionwas added dropwise
  2. customthe reaction temperature below 25° C.
  3. additionwas added
  4. customdecanted
  5. filtrationThe remaining solids were filtered
  6. washwashed several times with a total of 1 L of hot THF
  7. concentrationThe combined THF solution was concentrated
  8. dissolutiontwice dissolved in dichloromethane
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0e090eded2e84c55a5554270ba1d4aa8
Source dataset
uspto-grants-2004_01
Patent number
US06683183B2

Reaction notes

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