Sodium Thiosulfate → HCID 68039882, compound

HRID 920562Notes

Reaction equation

HRID 920562 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12]S[CH:10]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][S:32](=[O:36])(=[O:34])[CH:10]([C:14]2[CH:15]=[CH:16][C:17]([Br:20])=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 66653556HCID 66653556, compound

Product 1

HCID 68039882HCID 68039882, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-bromo-phenyl)-thiomorpholine-4-carboxylic acid tert-butyl ester (3.60 g; 10.05 mmol) in CH2Cl2 (100 mL) was added 3-chloroperoxybenzoic acid (5.20 g; 30.14 mmol), at 0° C. The resulting mixture was stirred overnight at RT, and subsequently, a saturated aqueous sodium thiosulfate solution was added and the mixture stirred for another 30 min. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined EtOAc layers were washed twice with an aqueous Na2CO3 solution. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford 2-(4-bromo-phenyl)-1,1-dioxo-1λ6-thiomorpholine-4-carboxylic acid tert-butyl ester (4.06 g) which was used as such in the next step.

Workup

  1. customat 0° C
  2. stirringthe mixture stirred for another 30 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with EtOAc
  5. washThe combined EtOAc layers were washed twice with an aqueous Na2CO3 solution
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87054bb8b34a4fa7b5b5c40bd6a40b8d
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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