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

HRID 1290284노트

반응식

HRID 1290284 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8900Heptane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cfb736df9da44a84ba9054c4904ae149
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750765

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