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

HRID 660980

反応式

HRID 660980 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9cb85568414d4ae69079bd087558d3c0
出典データセット
uspto-grants-2011_12
特許番号
US08084489B2

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