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

HRID 843703

反応式

HRID 843703 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-661d7440c50d4cb889d2b8072fdfdf67
出典データセット
uspto-grants-2002_04
特許番号
US06380189B1

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