Triphosgene → 1-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2-one

HRID 708167Notes

Reaction equation

HRID 708167 reaction equation
Br.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[N:13]=[C:14]([NH:16][C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19])[S:15][C:11]=3[CH2:10][CH2:9][O:8][C:7]=2[CH:22]=1.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[N:13]=[C:14]([N:16]4[C:17]([CH3:20])([CH3:21])[CH2:18][NH:19][C:24]4=[O:26])[S:15][C:11]=3[CH2:10][CH2:9][O:8][C:7]=2[CH:22]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 86652327N2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-2-methylpropane-1,2-diamine hydrobromide

Product 1

HCID 582042741-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2-oneYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the Example 356, N2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-2-methylpropane-1,2-diamine hydrobromide was reacted with triphosgene in tetrahydrofuran and purified on silicagel column eluting with 50% of ethyl acetate in heptane to give 1-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2-one. Yield 51%. MS(ESI+): 393.9

Workup

  1. custompurified on silicagel column
  2. washeluting with 50% of ethyl acetate in heptane

Sources & evidence

ORD record
ord-d34321bd72194924b9ac0f14dc833b82
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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