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

HRID 459487Notes

Reaction equation

HRID 459487 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-c3f225fd2c6e4cd88b80e4fa0adb7864
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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