N-(1-Hydroxy-2-methylpropan-2-yl)thiourea → 2-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-ylamino)-2-methylpropan-1-ol

HRID 708106Notes

Reaction equation

HRID 708106 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([NH2:9])=[S:8])([CH3:5])[CH3:4].Br[CH:11]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:13]=2[C:12]1=O>C(O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:13]2[C:12]3[N:9]=[C:7]([NH:6][C:3]([CH3:5])([CH3:4])[CH2:2][OH:1])[S:8][C:11]=3[CH2:17][CH2:16][O:15][C:14]=2[CH:18]=1

Participants

4

Reactant 2

HCID 22768414N-(1-Hydroxy-2-methylpropan-2-yl)thioureaHCID 579002754,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 582042622-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-ylamino)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.67 g (5.0 mmol) of 1-(1-hydroxy-2-methylpropan-2-yl)thiourea and 1.60 g (5.00 mmol) of 4,8-dibromo-3,4-dihydro-2Hbenzo[b]oxepin-5-one in 30 ml of ethanol was heated under reflux for 3 hours. The mixture was concentrated, the residue purified on silica gel column eluting the product with 10% of methanol in dichloromethane. Yield 1.38 g (75%). MS(ESI+): 369.3

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue purified on silica gel column
  5. washeluting the product with 10% of methanol in dichloromethane

Sources & evidence

ORD record
ord-93d8730cbb8345499cb59e46d93e85cd
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

Loading…