Hydrochloric Acid → Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

HRID 348796

Reaktionsgleichung

Reaktionsgleichung von HRID 348796
N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[ClH:21].N([O-])=O.[Na+].[S:26](=[O:28])=[O:27]>C(O)(=O)C.O>[Cl:21][S:26]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:28])=[O:27]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]BenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 22593631Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]-Benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate (XXXI, PREPARATION 10, 1.11 g, 4 mmol) is added to a mixture of water (5 mL) and concentrated hydrochloric acid (1 mL). Sodium nitrite (0.276 g, 4 mmol) is added to the mixture slowly at 0 degrees C. The mixture is then added to an acetic acid solution (5 mL) of CuCl2.2H2O saturated with sulfur dioxide. The mixture is stirred for 0.5 hours and poured into ice water. The mixture is extracted with ethyl acetate. The organic phase is separated and washed with saturated sodium bicarbonate, water, and saline and dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 8.69, 8.38, 8.20, 4.01, 3.49, 3.14, 1.72, 1.59, 1.01 and 0.79; MS (ESI+) for C15H2OClNO5S m/z (M+H)+=362.2

Aufarbeitung

  1. extractionThe mixture is extracted with ethyl acetate
  2. customThe organic phase is separated
  3. washwashed with saturated sodium bicarbonate, water, and saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7c1e868d36bd4791a0d9f46ba899644a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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