Hydrochloric Acid → 2-(1-Naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606607노트

반응식

HRID 1606607 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].C([N:18]([CH2:21][CH3:22])CC)C.COCCO[CH2:28][CH2:29]OC.Cl>O>[C:22]1([CH2:21][NH:18][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])[C:28]2[C:29](=[CH:10][CH:2]=[CH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8150DiglymeHCID 8471TriethylamineHCID 221013652,4-Dichloro-5-methanesulfonylbenzoic acid

생성물 1

HCID 215439942-(1-Naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2,4-Dichloro-5-methylsulfonylbenzoic acid (5.4 g.; 0.02 mole), 1-aminomethylnaphthylene (3.2 g.; 0.02 mole), and triethylamine (4 ml.) are added to diglyme (50 ml.). The resulting solution is refluxed with stirring for 4 hours. The reaction solution is cooled to room temperature and is slowly added to a solution of concentrated hydrochloric acid (10 ml.) in water (150 ml.) The aqueous layer is decanted from the viscous oil that separates. This viscous oil is dissolved in ethanol (25 ml.) and the resulting solution is poured into water. The tan colored solid which precipitates is collected and dried, yield 5.5 g. (70%). After several recrystallizations from acetonitrile, the 2-(1-naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid melts at 242°-246° C. (dec. with eff.).

후처리

  1. temperatureThe resulting solution is refluxed
  2. customis decanted from the viscous oil that separates
  3. dissolutionThis viscous oil is dissolved in ethanol (25 ml.)
  4. additionthe resulting solution is poured into water
  5. customThe tan colored solid which precipitates
  6. customis collected
  7. customdried
  8. customAfter several recrystallizations from acetonitrile

출처 및 근거

ORD 기록
ord-09d3f72c4529462690ad95685f89b234
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953476

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