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

HRID 1603006

Reaction equation

HRID 1603006 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 234445872-[3-(2,6-Dichlorophenyl)ureido]-5-iodobenzoic acidYield 59.3%

Reagents, catalysts & solvents 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fd94c897d4b94e37bbf90c7b3f105a4d
Source dataset
uspto-grants-1999_11
Patent number
US05985872

Linked notes

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