Phosgene → HCID 18690651, compound

HRID 1871184Notes

Reaction equation

C[Si](C)(C)[N:3]=[C:4]([C:22]1[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=1[F:32])[C:5]([C:11]1[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=1[F:21])=[N:6][Si](C)(C)C.[C:35](Cl)(Cl)=[O:36]>>[F:28][C:27]1[C:22]([C:4]2[C:5]([C:11]3[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=3[F:21])=[N:6][C:35](=[O:36])[N:3]=2)=[C:23]([F:32])[C:24]([F:31])=[C:25]([F:30])[C:26]=1[F:29]

Participants

Reactant 2

HCID 6371Phosgene

HCID 54352582HCID 54352582, compound

Product 1

HCID 18690651HCID 18690651, compoundYield 82%

Procedure

Analogous to Example 13, 5.33 g (10 mmol) of N,N'-bis(trimethylsilyl)-1,2-di(pentafluorophenyl)-ethanediimine, which was made in Example 2, was reacted with 10 mmol (1.0 g) of phosgene to yield 3.4 g (8.2 mmol, 82%) of 4,5-di(pentafluorophenyl)-2H-imidazol-2-one as a dark red solid. This product is also referred to as decafluorobenzilimidazolone. 3C[1H]NMR (δ; CDCl3) 177.6 ppm (>C=O--; s), 156.2 ppm (>C=N--; t, J3 =13.4 Hz), 112.6 ppm (i, t, J2 =23.6 Hz), 138.1 ppm (dt, J1 =254 Hz), 142.7 (dm, J1 =254 Hz), 144.5 ppm (dd, J1 =249 Hz). Elemental analysis was carried out: calcd (found) for C15F10N2O: C, 43.50% (43.57%), F, 45.87% (45.82%), N, 6.76% (6.71%), O, 3.86% (3.78%).

Sources & evidence

ORD record: ord-f63f9610f4c54a42a01cc78d5a9e9fab
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103459

Reaction notes

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