Tributyltin azide → HCID 178439708, compound

HRID 846222Notes

Reaction equation

HRID 846222 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[CH2:20][CH2:21][C:22]#[N:23])=[CH:15][CH:14]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].C([Sn]([N:44]=[N+:45]=[N-:46])(CCCC)CCCC)CCC>C1COCC1.CCOCC.Cl>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[CH2:20][CH2:21][C:22]3[NH:46][N:45]=[N:44][N:23]=3)=[CH:15][CH:14]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 4984872Tributyltin azideHCID 19884759HCID 19884759, compound

Product 1

HCID 178439708HCID 178439708, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The nitrile from Example 40, Step E, (1.0 g, 2.35 mmole) and tri-n-butyltin azide (1.0 g, 3.0 mmole) in dry THF (20 ml) were stirred at 70° for 48 hours, and then heated at reflux for 24 hours. The reaction mixture was cooled to room temperature, diluted with ether (20 ml) and concentrated HCl was added. After 1 hour, the solution was filtered, the solid was washed with ether and dried to yield the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. additionwas added
  4. filtrationthe solution was filtered
  5. washthe solid was washed with ether
  6. customdried

Sources & evidence

ORD record
ord-94b01216e98c4d6ebf645ab652332464
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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