Triethylamine → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

HRID 216704Notes

Reaction equation

HRID 216704 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.Cl.[NH:18]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]1>CN(C=O)C>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:18]2[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 12324096Thiomorpholine 1,1-dioxide hydrochloride

Product 1

HCID 523254684-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.18 ml (15.5 mmol) of triethylamine are added to a colorless suspension of 1.28 g (5 mmol) of 4-bromobenzyl bromide and 944 mg (5.5 mmol) thiomorpholine-1,1-dioxide hydrochloride in 15 ml DMF. After 3 h at RT, the reaction mixture is partitioned between CH2Cl2 and H2O. The aqueous phase is re-extracted four times with CH2Cl2. The combined organic extracts are washed with water, saturated brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo to afford, after drying in HV, the title compound which is used in the next step without further purification.

Workup

  1. customthe reaction mixture is partitioned between CH2Cl2 and H2O
  2. extractionThe aqueous phase is re-extracted four times with CH2Cl2
  3. washThe combined organic extracts are washed with water, saturated brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customto afford
  8. customafter drying in HV
  9. customthe title compound which is used in the next step without further purification

Sources & evidence

ORD record
ord-4defcdc8bc8e489dbdaa5316731a7b05
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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