Methanesulfonic Acid → HCID 59603090, compound

HRID 2068682Notes

Reaction equation

HRID 2068682 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)C1C=CC=CC=1.CS(O)(=O)=O>C(Cl)Cl>[CH2:21]([NH:20][C:18]([NH:17][C:15]1[S:16][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:23][C:13]=2[N:14]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59603105HCID 59603105, compound

Product 1

HCID 59603090HCID 59603090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-(benzyloxy)benzo[d]thiazol-2-yl)-3-ethylurea I (1.20 g, 3.66 mmol) in DCM (100.0 mL) was added methanesulfonic acid (4.32 mL, 66.22 mmol) and the resulting reaction mixture was stirred at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solvent was evaporated. The residue was cooled and then basified with saturated NaHCO3 solution followed by extraction with EtOAc (3×100 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated to obtain the desired product (0.90 g) that was carried forward to the next step without further purification. MS: 238.10 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of reaction (TLC monitoring)
  3. customthe solvent was evaporated
  4. temperatureThe residue was cooled
  5. extractionfollowed by extraction with EtOAc (3×100 mL)
  6. washThe combined organics was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eaa9e7fd523a4683b22b9f6f2aa89b85
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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