Hydrochloric Acid → HCID 178458105, compound

HRID 380988Notes

Reaction equation

HRID 380988 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-b2de6dafc18843398d0a0f83566334fd
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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