Hydrochloric Acid → 2-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606608ノート

反応式

HRID 1606608 の反応式
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[NH2:17][CH2:18][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+].Cl>O.C(COC)OC.C(N(CC)CC)C>[C:24]([C:22]1[O:23][C:19]([CH2:18][NH:17][C:2]2[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=1)([OH:26])=[O:25]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 221013652,4-Dichloro-5-methanesulfonylbenzoic acidHCID 568075445-(Aminomethyl)furan-2-carboxylic acid hydrochloride

生成物 1

HCID 215439632-(5-Carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 2,4-dichloro-5-methylsulfonylbenzoic acid (3.50 g.; 0.013 mole), 5-aminomethyl-2-furancarboxylic acid hydrochloride (4.83 g.; 0.027 mole), triethylamine (11.5 ml.), and glyme (25 ml.) is heated to 140°-150° C. for 24 hours. Solid sodium bicarbonate (5.0 g.) is added and refluxing is continued for another 24 hours. The mixture is poured into water (150 ml.) and acidified by the addition of 6N hydrochloric acid. The tan solid is collected, washed with water, and dried, 1.20 g., m.p. 269°-272° C. Recrystallization from acetonitrile gives 2-(5-carboxyfurfurylamino)-4-chloro-5-methylsulfonylbenzoic acid, m.p. 263.5°-265.5° C. (dec.).

後処理

  1. temperatureis heated to 140°-150° C. for 24 hours
  2. temperaturerefluxing
  3. customThe tan solid is collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetonitrile

出典と根拠

ORDレコード
ord-373033f9ef074426958868561f9e26ad
出典データセット
uspto-grants-1976_04
特許番号
US03953476

反応ノート

読み込み中…