HRID1457422

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID11465

N,N-Dimethyl-p-bromoaniline

C8H10BrN

HCID25517

未命名化合物

HCID615236

Trimethylsilyl p-toluenesulphonate

C10H16O3SSi

HCID5462224

Magnesium

结构：CC(C)(C)Oc1ccc(S(=O)c2ccc(OC(C)(C)C)cc2)cc1

HCID15389810

未命名化合物

PRODUCTS

生成物

结构：CN(C)c1ccc([S+](c2ccc(OC(C)(C)C)cc2)c2ccc(OC(C)(C)C)cc2)cc1.Cc1ccc(S(=O)(=O)[O-])cc1

HCID22290296

未命名化合物

收率 49%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of 8.5 grams (0.025 mol) of bis(4-tert-butoxyphenyl) sulfoxide in 300 grams of methylene chloride was cooled in an ice water bath. To the solution, 1.3 grams (0.013 mol) of triethylamine was added and 12.2 grams (0.05 mol) of trimethylsilyl-p-toluenesulfonate was added dropwise in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. A Grignard reagent, which was separately prepared in a conventional manner using 10.0 grams (0.05 mol) of 4-bromo-N,N-dimethylaniline, 1.2 grams (0.05 mol) of magnesium and 50 grams of THF, was added dropwise to the reaction solution in a controlled manner so that the temperature might not exceed 10° C. The reaction solution was ripened for 30 minutes while maintaining a reaction temperature of 0° to 10° C. 200 grams of an aqueous solution of 20% ammonium chloride was added to the reaction solution to terminate reaction. After separation, 200 grams of chloroform was added to the organic layer. After the organic layer was washed twice with 200 grams of water, the solvent was distilled off in vacuum, yielding an oily residue. The oily residue was recrystallized, isolating 7.6 grams (yield 49%) of bis(4-tert-butoxyphenyl)(4-dimethylaminophenyl)sul fonium p-toluenesulfonate with 99% purity.

WORKUP

后处理

customexceed 10° C
temperaturewhile maintaining a reaction temperature of 0° to 10° C
additionwas added dropwise to the reaction solution in a controlled manner so that the temperature might not
customexceed 10° C
waitThe reaction solution was ripened for 30 minutes
temperaturewhile maintaining a reaction temperature of 0° to 10° C
customto terminate
customreaction
customAfter separation, 200 grams of chloroform
additionwas added to the organic layer
washAfter the organic layer was washed twice with 200 grams of water
distillationthe solvent was distilled off in vacuum
customyielding an oily residue
customThe oily residue was recrystallized

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6a904b7894fa4ddf9fcd558bc89cebb4
来源数据集: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05847218
来源说明: uspto-grants-1998_12

反应 SMILES

[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[Si]([O:36][S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])(C)C.Br[C:48]1[CH:56]=[CH:55][C:51]([N:52]([CH3:54])[CH3:53])=[CH:50][CH:49]=1.[Mg].[Cl-].[NH4+]>C(Cl)Cl.C1COCC1>[C:43]1([CH3:46])[CH:42]=[CH:41][C:40]([S:37]([O-:39])(=[O:36])=[O:38])=[CH:45][CH:44]=1.[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S+:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)[C:48]2[CH:56]=[CH:55][C:51]([N:52]([CH3:54])[CH3:53])=[CH:50][CH:49]=2)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]