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

HRID 1606607ノート

反応式

HRID 1606607 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].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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-09d3f72c4529462690ad95685f89b234
出典データセット
uspto-grants-1976_04
特許番号
US03953476

反応ノート

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