Sulfuric Acid → N-(3-Hydroxy-2,6-dimethylphenyl)acetamide

HRID 579971

반응식

HRID 579971 반응식
[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7](N)[C:6]=1[CH3:13])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:15].N([O-])=O.[Na+].NC(N)=O.[Cl-].[Na+]>O>[C:1]([NH:4][C:5]1[C:6]([CH3:13])=[C:7]([OH:15])[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2]

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 5234Sodium ChlorideHCID 847848N-(3-amino-2,6-dimethylphenyl)acetamideHCID 23668193Sodium Nitrite

생성물 1

HCID 10419764N-(3-Hydroxy-2,6-dimethylphenyl)acetamide수율 67%

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

1-Acetamido-3-amino-2,6-dimethylbenzene (4.77 g; 26.8 mmol) was dissolved in a diluted acid prepared from concentrated sulfuric acid (3 ml) and water (30 ml). To the resulting solution was added dropwise a solution of sodium nitrite (2.40 g; 34.8 mmol) in water (5 ml) in a manner such that the temperature of the reaction mixture did not exceed 10° C. Then, the mixture was stirred under ice-cooling for 15 minutes. After addition of 1.00 g of urea (16.6 mmol), the mixture was dropwise added gradually into 75 ml of boiling water and the whole mixture was refluxed for 30 minutes. After cooling, sodium chloride was added, followed by extraction with ether and chloroform. The organic layer was washed with water and dried over magnesium sulfate (dehydration), and the solvent was distilled off to give 3.2 g (67%) of the title compound as colorless needles, m.p. 190°-195° C.

후처리

  1. customdid not exceed 10° C
  2. temperaturecooling for 15 minutes
  3. temperaturethe whole mixture was refluxed for 30 minutes
  4. temperatureAfter cooling
  5. extractionfollowed by extraction with ether and chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate (dehydration)
  8. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-678fdb5ec758429d970ca78ab89e6193
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04751232

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