Dichloromethane → N,N-Diethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)acetamide

HRID 1290284

反応式

HRID 1290284 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([OH:19])=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].ClCCl.S(Cl)(Cl)=O.[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28]>CCCCCCC.CN(C)C=O>[CH2:27]([N:29]([CH2:30][CH3:31])[C:17](=[O:19])[CH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=1)[CH3:28]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 27751103,5-Bis(1,1-dimethylethyl)-4-hydroxybenzeneacetic acid

生成物 1

HCID 18924148N,N-Diethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)acetamide収率 67.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8900Heptane溶媒2 回

実験手順

7.92 g (0.03 Mol) of (3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid are stirred overnight in 40 ml of heptane and 20 ml of dichloromethane with 4 ml of thionyl chloride and 4 drops of N,N-dimethylformamide. An additional 90 ml of heptane are added and then 90 ml of solvent and the excess amount of thionyl chloride are distilled off. The residual solution is cooled to room temperature and then 7.5 ml (0.072 mol) of diethylamine are added dropwise. The mixture is stirred one hour, then washed with water, 5% hydrochloric acid and water again. The solvent is evaporated in vacuo, and the residue is crystallized twice from acetonitrile to give 6.5 g of the intermediate product as colorless needles, melting at 111°-113° C.

後処理

  1. distillation90 ml of solvent and the excess amount of thionyl chloride are distilled off
  2. washwashed with water, 5% hydrochloric acid and water again
  3. customThe solvent is evaporated in vacuo
  4. customthe residue is crystallized twice from acetonitrile

出典と根拠

ORDレコード
ord-cfb736df9da44a84ba9054c4904ae149
出典データセット
uspto-grants-1998_05
特許番号
US05750765

関連ノート

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