Ammonia → HCID 57446112, compound

HRID 1803809Notes

Reaction equation

HRID 1803809 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([O:17][CH2:18][C:19]#[CH:20])[CH:14]=[CH:13][C:11]=2[N:12]=1)(=[O:7])=[O:6].N>CO>[CH2:18]([O:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([S:5]([NH2:4])(=[O:7])=[O:6])[S:9][C:10]=2[CH:16]=1)[C:19]#[CH:20]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59552643HCID 59552643, compound

Product 1

HCID 57446112HCID 57446112, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 500 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet was placed 2 (9 g, 27.8 mmol) and 200 mL of ammonia in methanol (7 N). The mixture was stirred at rt for 24 h. The solution was bubbled with air for 1 h and filtered. The filtrate was acidified with concentrated HCl to pH=2 and concentrated and dried. This solid was again treated with ammonia methanol solution (7 N, 200 mL) for 24 h at rt. The solution was bubbled with air for 1 h and filtered. The filtrate was added concentrated HCl to pH=2 and concentrated. It was filtered and the solid was washed with cooled water and dried to afford compound 3 as a yellow solid (5.2 g, 70%).

Workup

  1. customTo a 500 mL round bottomed flask equipped with a magnetic stir bar
  2. customThe solution was bubbled with air for 1 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried
  6. additionThis solid was again treated with ammonia methanol solution (7 N, 200 mL) for 24 h at rt
  7. customThe solution was bubbled with air for 1 h
  8. filtrationfiltered
  9. additionThe filtrate was added concentrated HCl to pH=2
  10. concentrationconcentrated
  11. filtrationIt was filtered
  12. washthe solid was washed with cooled water
  13. customdried

Sources & evidence

ORD record
ord-68adf5c7d23a417ba8a5f73d082a6b87
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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