Butyryl chloride → HCID 178454506, compound

HRID 267206Notes

Reaction equation

HRID 267206 reaction equation
[NH2:1][C:2]1[NH:7][CH2:6][C:5]2=[C:8]([CH3:14])[N:9]=[C:10]([CH2:11][CH2:12][CH3:13])[N:4]2[N:3]=1.[C:15]([Cl:20])(=[O:19])[CH2:16][CH2:17][CH3:18].[OH-].[Na+]>C(O)(=O)CCC>[ClH:20].[CH3:14][C:8]1[N:9]=[C:10]([CH2:11][CH2:12][CH3:13])[N:4]2[C:5]=1[CH2:6][NH:7][C:2]([NH:1][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[N:3]2

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 178440032HCID 178440032, compound

Product 1

HCID 178454506HCID 178454506, compound

Reagents, catalysts & solvents 1

HCID 264Butyric AcidSolvent

Procedure

2-Amino-3,4-dihydro-5-methyl-7-propylimidazo[ 5,1-f]-as-triazine (Example 1a) (2 g.) and butyryl chloride (11 ml.) in butyric acid (50 ml.) were heated under reflux for 5.5 hours and cooled with ice. 5N sodium hydroxide was added slowly and until the mixture was alkaline and the solid was filtered off. The filtrate was evaporated under reduced pressure and the residue was stirred with aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulphate, filtered and evaporated. The residue was crystallised from methanol to give a white solid, m.p. 161°-162°.

Workup

  1. temperatureunder reflux for 5.5 hours
  2. temperaturecooled with ice
  3. filtrationthe solid was filtered off
  4. customThe filtrate was evaporated under reduced pressure
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallised from methanol
  10. customto give a white solid, m.p. 161°-162°

Sources & evidence

ORD record
ord-5c1ca3af8f334503af7bdca2eb770c6b
Source dataset
uspto-grants-1976_03
Patent number
US03941785

Reaction notes

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