Water → 2-Aminomethyl-4-tert-butyl-6-iodophenol hydrochloride

HRID 437203

반응식

HRID 437203 반응식
[I:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].[Cl:13]C[C:15]([NH:17]CO)=O.O>C(O)(=O)C.S(=O)(=O)(O)O>[ClH:13].[NH2:17][CH2:15][C:4]1[CH:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=[C:2]([I:1])[C:3]=1[OH:12]

참가 물질

6

반응물 3

HCID 962WaterHCID 62466N-Methylol-alpha-chloroacetamideHCID 101715904-Tert-butyl-2-iodophenol

생성물 1

HCID 126342632-Aminomethyl-4-tert-butyl-6-iodophenol hydrochloride수율 36.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매

반응 조건

온도
20 °C

실험 절차

To a freshly prepared solution of 2-iodo-4-(1,1-dimethylethyl)phenol (5.5 g., 0.02 mole) in a mixture of acetic acid (27 ml.) and sulfuric acid (3 ml.) is added powdered 2-chloro-N-(hydroxymethyl)acetamide (2.5 g., 0.02 mole) with stirring at 20° C. over a 10 minute period. After 2.5 hours the orange solution is poured into water (200 ml.). The 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates is collected, dried by suction and dissolved in ethanol (75 ml.). Concentrated hydrochloric acid (15 ml.) is added and the mixture is refluxed for two hours. The mixture is concentrated to one-half its original volume and allowed to cool. The resulting precipitate (1.4 g.), which is unhydrolyzed 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]acetamide, is collected. The filtrate is concentrated to 25 ml. and, upon cooling, crude 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (4 g.) separates which upon crystallization from a mixture of ethanol and ether affords substantially pure 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (2.5 g.), m.p. 200°-201° (dec.).

후처리

  1. customThe 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates
  2. customis collected
  3. customdried by suction
  4. dissolutiondissolved in ethanol (75 ml.)
  5. additionConcentrated hydrochloric acid (15 ml.) is added
  6. temperaturethe mixture is refluxed for two hours
  7. concentrationThe mixture is concentrated to one-half its original volume
  8. temperatureto cool
  9. customis collected
  10. concentrationThe filtrate is concentrated to 25 ml
  11. temperatureand, upon cooling
  12. customupon crystallization
  13. additionfrom a mixture of ethanol and ether

출처 및 근거

ORD 기록
ord-3ca19eb14bad477a832d2c618a51c427
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04029816

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