Hydrochloric Acid → HCID 178458105, compound

HRID 720576Notes

Reaction equation

HRID 720576 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:18])[CH2:10][NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:5][CH:4]=1)#[N:2].[N:19]([Sn](CCCC)(CCCC)CCCC)=[N+:20]=[N-:21].Cl>>[NH:19]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([CH:9]([CH3:18])[CH2:10][NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:13])=[O:14])=[CH:5][CH:4]=2)=[N:2][N:21]=[N:20]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 21893419HCID 21893419, compound

Product 1

HCID 178458105HCID 178458105, compoundYield 89%

Procedure

0.2 g (0.8 mmol) of material from Example 53 and 0.5 g (1.5 mmol) of azidotributylstannane were heated to 80° C. for 72 hours. The mixture was cooled to ambient temperature, 5 mL of a saturated methanolic HCl solution was added, the mixture stirred for 30 minutes and was concentrated in vacuo. The residue was dissolved in 10 mL of acetonitrile and extracted four times with 5 mL each of hexane. The acetonitrile layer was concentrated in vacuo and the resulting solid was suspended in 10 mL of ethyl ether, filtered and dried in vacuo at 60° C. to afford 0.2 g (89%) of the title compound.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in 10 mL of acetonitrile
  3. extractionextracted four times with 5 mL each of hexane
  4. concentrationThe acetonitrile layer was concentrated in vacuo
  5. filtrationfiltered
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-255c118f4aa845a3a66ebf689f0f7553
Source dataset
uspto-grants-2006_11
Patent number
US07135487B2

Reaction notes

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