4,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one → N2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-2-methylpropane-1,2-diamine hydrobromide

HRID 708166Notes

Reaction equation

HRID 708166 reaction equation
[CH3:1][C:2]([NH:25][C:26]([NH2:28])=[S:27])([CH3:24])[CH2:3][NH:4]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:29][CH:30]1[CH2:36][CH2:35][O:34][C:33]2[CH:37]=[C:38]([Br:41])[CH:39]=[CH:40][C:32]=2[C:31]1=O>C(O)C>[BrH:29].[Br:41][C:38]1[CH:39]=[CH:40][C:32]2[C:31]3[N:28]=[C:26]([NH:25][C:2]([CH3:24])([CH3:1])[CH2:3][NH2:4])[S:27][C:30]=3[CH2:36][CH2:35][O:34][C:33]=2[CH:37]=1

Participants

4

Reactant 2

HCID 579002754,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-oneHCID 872499181-(2-Methyl-1-(tritylamino)propan-2-yl)thiourea

Product 1

HCID 86652327N2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-2-methylpropane-1,2-diamine hydrobromideYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the Example 356, 1-(2-methyl-1-(tritylamino)propan-2-yl)thiourea was reacted with 4,8-dibromo-3,4-dihydro-2Hbenzo[b]oxepin-5-one in ethanol under reflux for 18 hours to give N2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-2-methylpropane-1,2-diamine hydrobromide. Yield 68%. MS(ESI+): 368.0

Workup

  1. temperatureunder reflux for 18 hours

Sources & evidence

ORD record
ord-5c69a58c257840859d1bcbf923c19648
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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