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Triethylamine → 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate

HRID 434727
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HRID 434727 반응식
[OH:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[N:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[CH3:14].[C:19]([S:23][S:24][N:25]([C:27](F)=[O:28])[CH3:26])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.FC(NC)=O>C1(C)C=CC=CC=1>[C:19]([S:23][S:24][N:25]([CH3:26])[C:27](=[O:28])[O:13][C:9]1[CH:8]=[C:7]([CH3:14])[C:6]([N:5]=[CH:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[OH:1])=[C:11]([CH3:12])[CH:10]=1)([CH3:22])([CH3:21])[CH3:20]
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6

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HCID 8471Triethylamine2회HCID 12545956Methylcarbamyl fluorideHCID 20399612N-methyl-N-(tert-butylthiosulfenyl)carbamoyl fluorideHCID 1356896104-(2-Hydroxybenzylideneamino)-3,5-dimethylphenol2회

생성물 1

HCID 1361089684-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
50 °C

실험 절차

In a manner identical to that described in Example II, Part A, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol was prepared. To a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer and drying tube was added 4.83 grams (0.020 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol, 3.95 grams (0.020 moles) of N-(tertbutylthiosulfenyl)-N-fluorocarbonyl-N-methylamine, 2.12 grams (0.021 moles) of triethylamine and 200 milliliters of toluene. The resulting reaction mixture was heated to a temperature of 50° C. in an oil batch for 16 hours with continuous stirring. After this heating and stirring period, 1.0 grams (0.0041 moles) of N-tert-butylthiosulfenyl)-N-fluorocarbonyl-N-methylamine and 0.5 grams (0.005 moles) of triethylamine were added to the reaction mixture and heating continued for an additional 3 hours at a temperature of 50° C. with continuous stirring. The reaction mixture was cooled to room temperature and then washed twice with water, twice with a 2% aqueous sodium bicarbonate solution and once with a saturated brine solution. After drying the reaction mixture over magnesium sulfate, it was concentrated under reduced pressure to give a red oil. Purification of the red oil by column chromatography yielded 2.02 grams (0.0048 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate in the form of a yellow solid having a melting point of 121°-124° C. and the following structural formula: ##STR24##

후처리

  1. customwas prepared
  2. customTo a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer
  3. customdrying tube
  4. customThe resulting reaction mixture
  5. temperatureheating
  6. temperatureThe reaction mixture was cooled to room temperature
  7. washwashed twice with water, twice with a 2% aqueous sodium bicarbonate solution and once with a saturated brine solution
  8. dry with materialAfter drying the reaction mixture over magnesium sulfate, it
  9. concentrationwas concentrated under reduced pressure
  10. customto give a red oil
  11. customPurification of the red oil by column chromatography

출처 및 근거

ORD 기록
ord-17e22847a46647a48ef412682c4694c6
출처 데이터셋
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04399148

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