Hydrochloric Acid → HCID 86679503, compound

HRID 1776598Notes

Reaction equation

HRID 1776598 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[N:13]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[S:14]([CH3:17])(=[O:16])=[O:15].Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N:13]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[S:14]([CH3:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86679549HCID 86679549, compound

Product 1

HCID 86679503HCID 86679503, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)benzoate (0.902 g, theoric 2.314 mmol) in dioxane (23 ml), HCl 6N (4.63 ml, 27.8 mmol) was added, and the mixture was heated to 100° C. Additional HCl 6N (3.47 ml, 20.83 mmol) was added in two portion over 24 hours with stirring at the same temperature. The volatiles were removed under vacuum and the residue was dissolved in water (20 ml) and basified with NaHCO3 sat sol. (pH 7-8). The aqueous phase was washed with EtOAc and evaporated to dryness. The residue was purified by flash chromatography on silica gel column (DCM:MeOH=9:1 to 7:3) affording 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)benzoic acid (0.758 g, 2.115 mmol, 91% yield over two steps, MS/ESI+ 358.9 [MH]+).

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue was dissolved in water (20 ml)
  3. washThe aqueous phase was washed with EtOAc
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel column (DCM:MeOH=9:1 to 7:3)

Sources & evidence

ORD record
ord-8bbc5e832bec4d23ba2a576a04cd3731
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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