Tributyltin azide → HCID 178486015, compound

HRID 2303908Notes

Reaction equation

HRID 2303908 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([N+:23]([O-:25])=[O:24])=[C:12]([N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:13]=2)=[CH:5][CH:4]=1)#[N:2].[N:28]([Sn](CCCC)(CCCC)CCCC)=[N+:29]=[N-:30]>C1(C)C=CC=CC=1>[CH3:22][N:14]([C:12]1[CH:13]=[C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]3[NH:30][N:29]=[N:28][N:2]=3)=[CH:27][CH:26]=2)[CH:9]=[CH:10][C:11]=1[N+:23]([O-:25])=[O:24])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 18461286HCID 18461286, compound

Product 1

HCID 178486015HCID 178486015, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of t-butyl N-[5-(4-cyanophenoxy)-2-nitrophenyl]-N-methylcarbamate (2.95 g), azidotributyltin (7.97 g) and anhydrous toluene (30 ml) was heated at reflux for 23 hours. The reaction mixture was concentrated and then partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by reversed-phase liquid chromatography using water/acetonitrile=1/1 as the eluant to give the title compound (3.20 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 23 hours
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reversed-phase liquid chromatography

Sources & evidence

ORD record
ord-c9fabcc2c05b46e6bc87d54748c9ba98
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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