Methanesulfonic Acid → 1-ethyl-3-[5-hydroxy-7-[(E)-methoxyiminomethyl]-1,3-benzothiazol-2-yl]urea

HRID 712271Notes

Reaction equation

HRID 712271 reaction equation
C([O:8][C:9]1[CH:10]=[C:11](/[CH:24]=[N:25]/[O:26][CH3:27])[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[C:11](/[CH:24]=[N:25]/[O:26][CH3:27])=[CH:10][C:9]([OH:8])=[CH:23][C:13]=2[N:14]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 6395Methanesulfonic Acid2×HCID 872225011-ethyl-3-[7-[(E)-methoxyiminomethyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

Product 1

HCID 872225651-ethyl-3-[5-hydroxy-7-[(E)-methoxyiminomethyl]-1,3-benzothiazol-2-yl]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(E)-1-(5-(benzyloxy)-7-((methoxyimino)methyl)benzo[d]thiazol-2-yl)-3-ethylurea (325 mg, 0.85 mmol) was stirred in DCM (17 ml) and methanesulfonic acid (2.8 ml) was added. The reaction was allowed to stir at rt for 1 h in a round bottomed flask equipped with a drying tube. LCMS showed a mixture of product and starting material and the reaction was stirred for a further 1 h and LCMS showed no further reaction. Methanesulfonic acid (0.5 ml) was added and the reaction stirred for 18 h, diluted with DCM (30 ml) and extracted with water (2×25 ml). The DCM layer contained mainly starting material and impurities by LCMS. The aqueous portions were combined, and solid sodium hydrogen carbonate was used to adjust the pH to ˜10 and then extracted with a 1:1 mixture of DCM-Et2O. The combined organic extracts were washed with water, dried (MgSO4) and concentrated to afford a yellow solid (100 mg, 80% purity by LC-MS) (40%) which was used directly in the next step.

Workup

  1. customequipped with a drying tube
  2. additiona mixture of product
  3. stirringthe reaction was stirred for a further 1 h
  4. customno further reaction
  5. stirringthe reaction stirred for 18 h
  6. extractionextracted with water (2×25 ml)
  7. extractionextracted with a 1:1 mixture of DCM-Et2O
  8. washThe combined organic extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto afford a yellow solid (100 mg, 80% purity by LC-MS) (40%) which

Sources & evidence

ORD record
ord-4f833fe8e3ea405f92b774e344b510be
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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