Azidotrimethylsilane → HCID 136120916, compound

HRID 2270897Notes

Reaction equation

HRID 2270897 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-a086b3213ce64b70bdaa9c57e534ca84
Source dataset
uspto-grants-2001_12
Patent number
US06333296B1

Reaction notes

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