4-[(2-Methylthio-ethyl)-(2-methoxy-benzoyl)-amino]-benzenesulfonamide → 4-[(2-Methylthio-ethyl)-(2-methoxy-benzyl)-amino]-benzenesulfonamide

HRID 1789659Notes

Reaction equation

HRID 1789659 reaction equation
B.C1COCC1.C1COCC1.[CH3:12][S:13][CH2:14][CH2:15][N:16]([C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35])[C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>C1COCC1>[CH3:12][S:13][CH2:14][CH2:15][N:16]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35])[C:17]1[CH:18]=[CH:19][C:20]([S:23]([NH2:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 220362164-[(2-Methylthio-ethyl)-(2-methoxy-benzoyl)-amino]-benzenesulfonamideHCID 178419153HCID 178419153, compound

Product 1

HCID 220361674-[(2-Methylthio-ethyl)-(2-methoxy-benzyl)-amino]-benzenesulfonamideYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 M BH3.THF/THF (6.8 mL, 6.8 mmol) was added to a solution of 4-[(2-methylthio-ethyl)-(2-methoxy-benzoyl)-amino]-benzenesulfonamide (0.51 g, 1.34 mmol) in THF (5 mL). After 18 h, the excess BH3 was quenched by addition of 0.1 M HCl; followed by partitioning the mixture between CH2Cl2 and NaHCO3. The organic layer was dried (Na2SO4), filtered, evaporated in vacuo, and the residue was purified by MPLC (CH2Cl2 to 70:30 CH2Cl2/EtOAc) to afford 0.38 g (77%) of 4-[(2-methylthio-ethyl)-(2-methoxy-benzyl)-amino]-benzenesulfonamide as a clear glass.

Workup

  1. customthe excess BH3 was quenched by addition of 0.1 M HCl
  2. customby partitioning the mixture between CH2Cl2 and NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue was purified by MPLC (CH2Cl2 to 70:30 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-e17c250301514e26be8bfcb2abe5b00e
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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