Formaldehyde → 3-[(2-Methoxyethyl)(methyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 747541Notes

Reaction equation

HRID 747541 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([OH:11])=[O:10].C=O.[BH4-].[Na+].F[C:25](F)(F)C(O)=O.OS(O)(=O)=O>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:25])[C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:16])=[O:17])[C:9]([OH:11])=[O:10]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 691167263-[(2-Methoxyethyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 691177853-[(2-Methoxyethyl)(methyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, 1.0 g (3 mmol) of 3-[(2-methoxyethyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid was dissolved in 150 ml of THF, and 10 g of paraformaldehyde and then, a little at a time, 0.7 g (20 mmol) of NaBH4 were added. 15 ml of trifluoroacetic acid were then slowly added dropwise. The mixture was stirred at RT for another 3 days. For work-up, 10% strength H2SO4 was added, and the mixture was extracted repeatedly with EA and then dried over MgSO4 and concentrated. This gave a brownish oil.

Workup

  1. extractionthe mixture was extracted repeatedly with EA
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThis gave a brownish oil

Sources & evidence

ORD record
ord-2809dc99cb6842e1999bc37d719c7038
Source dataset
uspto-grants-2008_07
Patent number
US07396939B2

Reaction notes

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