Water → 3-Chloro-4-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoic acid

HRID 1808177Notes

Reaction equation

HRID 1808177 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[H-].[Na+].[Cl:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=1[S:31](Cl)(=[O:33])=[O:32])[C:24]([O:26]C)=[O:25].O>C1COCC1>[Cl:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=1[S:31]([N:6]([CH2:5][C:4]1[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:3]=1[O:2][CH3:1])[C:7]1[S:8][CH:9]=[CH:10][N:11]=1)(=[O:33])=[O:32])[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 47002988Methyl 3-chloro-4-(chlorosulfonyl)benzoateHCID 49931979N-(2,4-dimethoxybenzyl)thiazol-2-amine

Product 1

HCID 577320313-Chloro-4-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of N-(2,4-dimethoxybenzyl)-1,3-thiazol-2-amine (Preparation 6, 8.4 g, 33.4 mmol, 1 eq) in THF (80 ml) was added 60% sodium hydride (2.0 g, 50.2 mmol, 1.5 eq) portionwise. The mixture was stirred for 15 minutes before the addition of methyl 3-chloro-4-(chlorosulfonyl)benzoate (Preparation 5, 9 g, 33.4 mmol, 1 eq) then stirred for a further 30 minutes. The reaction mixture was added to water (20 ml) and the THF evaporated in vacuo. The residue was diluted with water (200 ml), extracted with ethyl acetate (2×200 ml) and DCM (100 ml). The combined organics were dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound.

Workup

  1. customthe THF evaporated in vacuo
  2. additionThe residue was diluted with water (200 ml)
  3. extractionextracted with ethyl acetate (2×200 ml) and DCM (100 ml)
  4. dry with materialThe combined organics were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad2c5b8aac5e40d096d1d855d840f41f
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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