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

HRID 1606608노트

반응식

HRID 1606608 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8471Triethylamine용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-373033f9ef074426958868561f9e26ad
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953476

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