Azidotrimethylsilane → HCID 136120916, compound

HRID 1017173Notes

Reaction equation

HRID 1017173 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-98162febc60d43e38b1436a450c3abec
Source dataset
uspto-grants-2002_11
Patent number
US06479435B1

Reaction notes

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