Methanesulfonyl chloride → HCID 178524175, compound

HRID 1406463Notes

Reaction equation

HRID 1406463 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=S.C([O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)C.CS(Cl)(=O)=O>ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:19]2[CH:20]=[CH:21][C:16]([C:15]([OH:24])=[O:14])=[CH:17][C:18]=2[N:23]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 458855Ethyl 3,4-Diaminobenzoate

Product 1

HCID 178524175HCID 178524175, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1,3-dichloro-2-isothiocyanato-benzene (4.50 g, 22.1 mmol) in 50 mL dichloromethane was added to a stirred solution of 3,4-diamino-benzoic acid ethyl ester (4.00 g, 22.2 mmol) in 100 mL dichloromethane. After stirring for 2 days the mixture was concentrated i.vac. The residue was taken up in 200 mL dichloromethane. TEA (7.0 mL, 49.9 mmol) and DMAP (100 mg, 0.8 mmol) were added. A mixture of methanesulfonyl chloride (1.70 mL, 22.0 mmol) in 50 mL dichloromethane was added to the solution and stirred overnight. The mixture was concentrated i.vac. The residue was taken up in methanol and 4 M NaOH (aq) was added. After stirring overnight at ambient temperature the mixture was heated to reflux for 2 h and concentrated i.vac. The residue was taken up in water and methanol and neutralized with HCl (aq). The mixture was filtered and washed with water.

Workup

  1. concentrationwas concentrated i.vac
  2. additionwas added to the solution
  3. stirringstirred overnight
  4. concentrationThe mixture was concentrated i.vac
  5. addition4 M NaOH (aq) was added
  6. stirringAfter stirring overnight at ambient temperature the mixture
  7. temperaturewas heated
  8. temperatureto reflux for 2 h
  9. concentrationconcentrated i.vac
  10. filtrationThe mixture was filtered
  11. washwashed with water

Sources & evidence

ORD record
ord-4112bf8004364724b559daf36cef20f6
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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