Triethylamine → Methyl 2-amino-4-{[(methylsulfonyl)amino]methyl}benzoate

HRID 1816539Notes

Reaction equation

HRID 1816539 reaction equation
[Cl-].[NH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH2:6][NH3+:7].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>CC(N(C)C)=O>[NH2:2][C:3]1[CH:4]=[C:5]([CH2:6][NH:7][S:23]([CH3:22])(=[O:25])=[O:24])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11298899HCID 11298899, compound

Product 1

HCID 11288376Methyl 2-amino-4-{[(methylsulfonyl)amino]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

3 g of 3-amino-4-methoxycarbonylbenzylammonium chloride (18.8 mmol) are dissolved in 50 ml of dimethylacetamide, triethylamine (2.8 g, 27.7 mmol) is added, and the mixture is subsequently reacted at 0-10° C. with a solution of methanesulfonyl chloride (1.6 g, 13.8 mmol) in 20 ml of dimethylacetamide. After 1 h, the solvent is removed in vacuo and the residue is worked up by extraction with water/dichloromethane. The combined organic extracts are washed with water and dried (Na2SO4) and then evaporated on a rotary evaporator. The residue obtained is crystallized from water, whereupon 3 g (84%) of methyl 2-amino-4-methanesulfonylaminomethylbenzoate of melting point 120-121° C. are obtained.

Workup

  1. customthe solvent is removed in vacuo
  2. extractionthe residue is worked up by extraction with water/dichloromethane
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated on a rotary evaporator
  6. customThe residue obtained
  7. customis crystallized from water, whereupon 3 g (84%) of methyl 2-amino-4-methanesulfonylaminomethylbenzoate of melting point 120-121° C.
  8. customare obtained

Sources & evidence

ORD record
ord-cc36037be39b4bb7aa453d178085f0a4
Source dataset
uspto-grants-2005_04
Patent number
US06884903B2

Reaction notes

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