Azido(trimethyl)stannane → 2-(4,4-Dimethyl-cyclohex-1-enyl)-4-(1-trimethylstannanyl-1H-tetrazol-5-ylmethyl)-phenylamine

HRID 1711308Notes

Reaction equation

HRID 1711308 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[C:11]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:12]=1.[N:19]([Sn:22]([CH3:25])([CH3:24])[CH3:23])=[N+:20]=[N-:21]>C1(C)C=CC=CC=1>[CH3:17][C:14]1([CH3:18])[CH2:15][CH2:16][C:11]([C:3]2[CH:4]=[C:5]([CH2:8][C:9]3[N:19]([Sn:22]([CH3:25])([CH3:24])[CH3:23])[N:20]=[N:21][N:10]=3)[CH:6]=[CH:7][C:2]=2[NH2:1])=[CH:12][CH2:13]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 58754882[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-acetonitrile

Product 1

HCID 587548812-(4,4-Dimethyl-cyclohex-1-enyl)-4-(1-trimethylstannanyl-1H-tetrazol-5-ylmethyl)-phenylamineYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of [4-amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-acetonitrile (as prepared in the previous step, 417 mg, 1.73 mmol) and azidotrimethylstannane (428 mg, 2.08 mmol) in toluene (8 mL) was heated at reflux for 40 h. The reaction was allowed to cool to room temperature and then filtered. The precipitate was washed with 20 mL of toluene and dried under vacuum to afford 410 mg (53%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C16H21N5, 284.1 (M-SnMe3+2H), found 284.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 h
  3. filtrationfiltered
  4. washThe precipitate was washed with 20 mL of toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-680998fe02af42dbbc8e33c44bb446d6
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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