Hydrochloric Acid → 4-methoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide

HRID 619066

反応式

HRID 619066 の反応式
Br.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:17][C:14]2[S:15][CH:16]=[C:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)[N:13]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 28030374-(2-Naphthyl)-thiazol-2-ylamine hydrobromide

生成物 1

HCID 103407094-methoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide収率 29.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 0.5 g of 4-(2-naphthyl)-thiazol-2-ylamine hydrobromide with 0.34 g of 4-methoxy-benzenesulfonyl chloride was stirred for 3 hours with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and freed from solvent. The residue was dissolved in a mixture of 25 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 10 ml of ethyl acetate and 15 ml of n-hexane yielded 0.19 g of 4-methoxy-N-(4-naphthalen-2-yl-thiazol-2-yl)-benzenesulfonamide as colorless crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried with magnesium sulphate
  3. dissolutionThe residue was dissolved in a mixture of 25 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.5 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. customThe product separated upon neutralization with concentrated hydrochloric acid
  7. customRecrystallization from 10 ml of ethyl acetate and 15 ml of n-hexane

出典と根拠

ORDレコード
ord-5fa11970a696472ab5607fde3a83f943
出典データセット
uspto-grants-1999_09
特許番号
US05958910

関連ノート

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