Hydrochloric Acid → HCID 131721513, compound

HRID 612383Notes

Reaction equation

HRID 612383 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([S:16](Cl)(=[O:18])=[O:17])[CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[NH:25]1[CH2:30]C[O:28]CC1.[OH-:31].[Na+].Cl>O1CCOCC1>[N:11]1([C:30]([NH2:25])=[O:31])[CH2:10][CH2:5][O:4][CH2:3][CH2:20]1.[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([S:16]([OH:28])(=[O:18])=[O:17])[CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 23221647HCID 23221647, compound

Product 1

HCID 131721513HCID 131721513, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2,4-Dichlorophenoxy)-4-methylsulphonylaminobenzene-sulphonic acid chloride (1.36 g, 3.2 mmol) was dissolved in dioxan (5 ml) and at 0° C. added dropwise to a solution of morpholine (2.25 ml, 25.6 mmol) in 1N aqueous NaOH (26 ml, 26 mmol) and dioxan (20 ml). The mixture was stirred for 1 hour at 0° C., acidified with 1N HCl and extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and the solvent was evaporated off. The residue was purified by chromatography (silica gel, CH2Cl2 /ethyl acetate 9/1). Yield: 0.93 g=60% 13C (100 MHz, DMSO-d6) δ 150.02, 147.15, 133.44, 130.43, 129.51, 129.31, 129.18, 126.23, .125.98, 123.95, 123.02, 122.51, 116.78, 115.83, 65.41, 45.83, 41.03

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvent was evaporated off
  4. customThe residue was purified by chromatography (silica gel, CH2Cl2 /ethyl acetate 9/1)

Sources & evidence

ORD record
ord-0a6fb0b29ab8454997dea205491da628
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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