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

HRID 588225Notes

Reaction equation

HRID 588225 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-67cb1db00c0e4657ae12a18377c64d85
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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