Azidotrimethylsilane → HCID 136120916, compound

HRID 380296Notes

Reaction equation

HRID 380296 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([N:15]=[C:16]=[O:17])=[C:4]([F:18])[CH:3]=1.C[Si]([N:23]=[N+:24]=[N-:25])(C)C>>[Cl:1][C:2]1[C:7]([O:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][C:5]([N:15]2[C:16](=[O:17])[NH:25][N:24]=[N:23]2)=[C:4]([F:18])[CH:3]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 11323074HCID 11323074, compound

Product 1

HCID 136120916HCID 136120916, compound

Procedure

4-Chloro-2-fluoro-5-(2-pyrimidyloxy)phenylisocyanate (0.96 g) and trimethylsilyl azide (5 ml) were heated at reflux overnight under nitrogen. The reaction mixture was processed and the resulting oil chromatographed on silica gel eluting with ethyl acetate:methylene chloride, 1:4, to give a yellow semi-solid (0.54 g). 1H NMR (CDCl3, TMS): 7.16(1H, dd, J=4.8 Hz), 7.49(1H, d, J=9.3 Hz), 7.64(1H, d, J=6.8 Hz), 8.59(2H, d, J=4.8 Hz).

Workup

  1. temperatureat reflux overnight under nitrogen
  2. customthe resulting oil chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-d541c9618e2b4651aef8680f45c79e12
Source dataset
uspto-grants-2001_10
Patent number
US06303543B1

Reaction notes

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