Water → 2-(4-Bromo-phenyl)-thiomorpholin-3-one

HRID 2167850Notes

Reaction equation

HRID 2167850 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].C([O-])([O-])=O.[K+].[K+].C([O:14][C:15](=O)[CH:16](Br)[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)C.O>CCO>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH:16]2[S:5][CH2:4][CH2:3][NH:2][C:15]2=[O:14])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9082Cysteamine HydrochlorideHCID 11430Potassium CarbonateHCID 12754876Ethyl 2-bromo-(4-bromophenyl)acetate

Product 1

HCID 666540542-(4-Bromo-phenyl)-thiomorpholin-3-oneYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-aminoethanethiol hydrochloride (6.93 g; 61 mmol) in EtOH (400 mL) was added K2CO3 (16.86 g; 122 mmol), at RT, followed after 15 minutes by bromo-(4-bromo-phenyl)-acetic acid ethyl ester (12 mL; 61 mmol). The resulting mixture was stirred at RT for two days, subsequently, water was added and the resulting mixture was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was recrystallized from EtOH to afford 2-(4-bromo-phenyl)-thiomorpholin-3-one (12.8 g).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from EtOH

Sources & evidence

ORD record
ord-b8e37af2ebfe49bea1e889399c266e3a
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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