Pyridine → HCID 59377779, compound

HRID 1691823Notes

Reaction equation

HRID 1691823 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[NH2:20].N1C=CC=CC=1.[C:27](Cl)(Cl)=[O:28]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[C:3]([N:20]=[C:27]=[O:28])=[CH:4][C:5]([O:9][CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:14])[CH3:15])=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 593778662-Bromo-4-chloro-5-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethoxy]benzenamine

Product 1

HCID 59377779HCID 59377779, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-chloro-phenylamine (0.15 g, 0.393 mmol) in toluene (3 ml) was added pyridine (0.038 ml, 0.472 mmol), DMAP (0.048 g, 0.393 mmol) and 20% phosgene in toluene (0.224 ml, 0.433 mmol). The mixture was stirred at room temperature for two hours. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure to give [2-(4-bromo-2-chloro-5-isocyanato-phenoxy)-ethoxy]-tert-butyl-dimethyl-silane (0.155 g) as a white solid, which was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ae84dae7816d4fa79b17e7937179e80c
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

Loading…