Hydrochloric Acid → 2-[3-(2,6-Dichlorophenyl)ureido]-5-iodobenzoic acid

HRID 1603006

Reaktionsgleichung

Reaktionsgleichung von HRID 1603006
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]=[C:26]=[O:27].Cl>O1CCOCC1.O>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[NH:25][C:26](=[O:27])[NH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 516892Sodium BicarbonateHCID 6045371,3-Dichloro-2-isocyanatobenzene

Produkt 1

HCID 234445872-[3-(2,6-Dichlorophenyl)ureido]-5-iodobenzoic acidAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To an ice cooled solution of 2-amino-5-iodobenzoic acid (540 mg, 2.03 mmol) and sodium bicarbonate (170 mg, 2.03 mmol) in 9 mL of dioxane/water (2:1) was added 2,6-dichlorophenylisocyanate (468 mg, 2.44 mmol). The reaction was slowly warmed to room temperature while stirring overnight. The reaction mixture was acidified with 2N HCl and extracted with EtOAc. The product, which partially precipitated from the organic layer, was filtered and washed with EtOAc (173 mg). The filtrate was dried (MgSO4) and evaporated under reduced pressure. Trituration of the residue with Et2O afforded an additional 543 mg of 2-[3-(2,6-dichlorophenyl)ureido]-5-iodobenzoic acid: 1H-NMR (300 MHz, d6 -DMSO) δ 7.37 (t, J=8 Hz, 1H), 7.58 (d, J=8 Hz, 2H), 7.84 (dd, J=8 Hz, 4 Hz, 1H), 8.19 (d, J=4 Hz, 1H), 8.28 (d, J=8 Hz, 1H), 9.60 (s, 1H, exchangeable), 10.50 (s, 1H, exchangeable).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe product, which partially precipitated from the organic layer
  3. filtrationwas filtered
  4. washwashed with EtOAc (173 mg)
  5. dry with materialThe filtrate was dried (MgSO4)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd94c897d4b94e37bbf90c7b3f105a4d
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985872

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