Sodium ethanethiolate → HCID 70178576, compound

HRID 2227390Notes

Reaction equation

HRID 2227390 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([S-])C.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 46180457HCID 46180457, compound

Product 1

HCID 70178576HCID 70178576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Methoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (8.21 g, 0.023 mol) and sodium ethanethiolate (3.9 g, 0.046 mol) were heated in DMF (50 mL) at reflux under Ar for 1 h, then concentrated in vacuo to remove a portion of the DMF. The residue was added to ice-H2O and extracted with EtOAc (3×). The aqueous basic layer was acidified with 1N HCl and extracted with EtOAc (4×100 mL). The organic layers were combined, washed with H2O (2×), brine, and dried (Na2SO4). Filtration and concentration in vacuo gave the title compound. 1H NMR (CDCl3) δ 7.40 (t, 1H, J=8 Hz), 7.27-7.29 (m, 1H), 7.22 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=2, 5 Hz), 6.21 (br s, 1H), 3.51 (t, 2H, J=5 Hz), 2.98 (t, 2H, J=5 Hz), 1.42 (s, 9H).

Workup

  1. temperatureat reflux under Ar for 1 h
  2. concentrationconcentrated in vacuo
  3. customto remove a portion of the DMF
  4. additionThe residue was added to ice-H2O
  5. extractionextracted with EtOAc (3×)
  6. extractionextracted with EtOAc (4×100 mL)
  7. washwashed with H2O (2×), brine
  8. dry with materialdried (Na2SO4)
  9. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-6b674b7f354a4f5586d69587567c4058
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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