Hydrogen Bromide → 5,6-Dihydro-4H-pyrrolo[3,4-d]thiazole Hydrobromide

HRID 546433Notes

Reaction equation

HRID 546433 reaction equation
C1(S([N:10]2[CH2:17][C:16]3[S:15][CH:14]=[N:13][C:12]=3[CH2:11]2)(=O)=O)C=CC=CC=1.C1(O)C=CC=CC=1.[BrH:25].C(OCC)(=O)C>O>[BrH:25].[S:15]1[C:16]2[CH2:17][NH:10][CH2:11][C:12]=2[N:13]=[CH:14]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 996PhenolHCID 8857Ethyl AcetateHCID 184428065-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

Product 1

HCID 184427795,6-Dihydro-4H-pyrrolo[3,4-d]thiazole Hydrobromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole (800 mg), phenol (800 μl) and 47% hydrobromic acid (5.00 ml) was heated under reflux for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to conduct liquid separation. The resultant water layer was concentrated under reduced pressure. Ethyl acetate was added to the residue, colorless powder deposited was collected by filtration to obtain the title compound (521 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customliquid separation
  4. concentrationThe resultant water layer was concentrated under reduced pressure
  5. additionEthyl acetate was added to the residue, colorless powder
  6. filtrationdeposited was collected by filtration

Sources & evidence

ORD record
ord-9d2b7fda0ab04235b69314818d1d2e51
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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