Azidotrimethylsilane → HCID 136120916, compound

HRID 1953979Notes

Reaction equation

HRID 1953979 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-ed04cd2ce2544b52bda55e3692e24ca7
Source dataset
uspto-grants-2000_09
Patent number
US06121201

Reaction notes

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