Hydrochloric Acid → HCID 131732709, compound

HRID 1468905Notes

Reaction equation

HRID 1468905 reaction equation
[NH2:1][C:2]1[C:12]([I:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:14][CH3:15])[CH:3]=1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].Cl>C(Cl)Cl>[I:13][C:12]1[C:2]([N:1]([S:24]([CH3:23])(=[O:26])=[O:25])[S:24]([CH3:23])(=[O:26])=[O:25])=[CH:3][C:4]([S:14][CH3:15])=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 89815347HCID 89815347, compound

Product 1

HCID 131732709HCID 131732709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-amino-5-iodo-2-(methylthio)benzoate (13.6 g, 40 mmol) in DCM (100 mL) was added Et3N (13.8 mL, 100 mmol), followed by MsCl (7.7 mL, 100 mmol) at 0° C. After addition the mixture was stirred at rt for 2 h. 1N HCl solution (50 mL) was added to the mixture and the aqueous phase was extracted with DCM (1×100 mL). The organic solution was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give ethyl 5-iodo-4-(N-(methylsulfonyl)methylsulfonamido)-2-(methylthio)benzoate.

Workup

  1. additionAfter addition the mixture
  2. extractionthe aqueous phase was extracted with DCM (1×100 mL)
  3. washThe organic solution was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-157a95060c1c45348c586210d57f2648
Source dataset
uspto-grants-2015_04
Patent number
US09006244B2

Reaction notes

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