Acetic Acid → 2,5-dimethyl-4-iodo-N-isopropyl-aniline

HRID 1017796노트

반응식

HRID 1017796 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][C:12]([CH3:14])=O.C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>O1CCCC1.O>[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH:4][CH:12]([CH3:14])[CH3:11]

참가 물질

10

반응물 7

HCID 176Acetic AcidHCID 180AcetoneHCID 280Carbon DioxideHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)AmineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 184052092,5-dimethyl-4-iodo-N-isopropyl-aniline

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

4.1 g (0.017 mol) of 2,5-dimethyl-4-iodo-aniline, 1.4 ml of (0.019 mol) of acetone, 1.4 ml of (0,024 mol) of glacial acetic acid and 0.1 g (0.001 mol) of p-toluenesulphonic acid are dissolved in 30 ml of tetrahydrofuran and stirred for 30 minutes at ambient temperature. Then 4.7 g (0.022 mol) of sodium triacetoxyborohydride are added and the mixture is stirred for another 20 hours at ambient temperature. After the addition of 150 ml of water, sodium carbonate is added until no further development of CO2 can be detected. The mixture is then extracted with ethyl acetate, the combined organic extracts are dried over sodium sulphate and evaporated down. The residue is chromatographed on silica gel, eluting with ethyl acetate/petroleum ether (2:98).

후처리

  1. stirringthe mixture is stirred for another 20 hours at ambient temperature
  2. extractionThe mixture is then extracted with ethyl acetate
  3. dry with materialthe combined organic extracts are dried over sodium sulphate
  4. customevaporated down
  5. customThe residue is chromatographed on silica gel
  6. washeluting with ethyl acetate/petroleum ether (2:98)

출처 및 근거

ORD 기록
ord-9ea8e5ce66f345f3a5ed97bf6d513831
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479524B1

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