Triethylamine → dimethyl-thiocarbamic acid O-(4'-tert-butyl-2,6-dimethyl-biphenyl-4-yl)ester

HRID 660980

반응식

HRID 660980 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=2[CH3:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[S:30]>O1CCOCC1.CN(C)C1C=CN=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH3:19])=[CH:13][C:14]([O:18][C:29](=[S:30])[N:28]([CH3:32])[CH3:27])=[CH:15][C:16]=2[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 533020184'-Tert-butyl-2,6-dimethylbiphenyl-4-OL

생성물 1

HCID 86625171dimethyl-thiocarbamic acid O-(4'-tert-butyl-2,6-dimethyl-biphenyl-4-yl)ester수율 95.8%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 4′-tert-butyl-2,6-dimethyl-biphenyl-4-ol (10 g, 37.3 mmol) in dioxane (157 ml) is added 4-dimethylaminopyridine (476 mg, 3.9 mmol), triethylamine (10 mL, 78.6 mmol), and dimethylthiocarbamoyl chloride (6.1 g, 49.1 mmol). The reaction mixture is heated to reflux overnight. After cooling to rt, the reaction mixture is partitioned between ethyl acetate and water. The aqueous layer is back-extracted with ethyl acetate, and the combined organic layers are dried and concentrated. The resulting residue is applied to silica gel and eluted using 20% ethyl acetate in hexanes to give dimethyl-thiocarbamic acid O-(4′-tert-butyl-2,6-dimethyl-biphenyl-4-yl)ester (12.2 g).

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe reaction mixture is partitioned between ethyl acetate and water
  4. extractionThe aqueous layer is back-extracted with ethyl acetate
  5. customthe combined organic layers are dried
  6. concentrationconcentrated
  7. washeluted

출처 및 근거

ORD 기록
ord-9cb85568414d4ae69079bd087558d3c0
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084489B2

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