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Triethylamine → alpha,alpha,alpha-trifluoro-N-[[8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl]methyl]-p-toluamide

HRID 67688
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HRID 67688 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1Cl)[C:5]([NH:7][CH2:8][C:9]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1)=[O:6].C(N(CC)CC)C.[F:33][C:34]([F:45])([F:44])C1C=CC(C(Cl)=O)=CC=1>C1COCC1>[F:33][C:34]([F:45])([F:44])[C:24]1[CH:23]=[CH:22][C:4]([C:5]([NH:7][CH2:8][C:9]2([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH2:10]2)=[O:6])=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 130520413,4-Dichloro-N-[(8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

생성물 1

HCID 13052044alpha,alpha,alpha-trifluoro-N-[[8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl]methyl]-p-toluamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1.0 g (0.00465 mole) of the ketal from Example 1, part A and 0.47 g (0.65 ml) of triethylamine in 15 ml of THF was cooled in an ice bath. To this cooled solution there was added a solution of 0.97 g (0.00465 mole) of p-trifluoromethylbenzoyl chloride in 10 ml of THF over 10 minutes while stirring. The mixture was placed in a refrigerator overnight. Upon removal from the refrigerator, the bulk of the solvent was removed on a rotary evaporator. The residue was taken up in diethyl ether and aqueous sodium bicarbonate solution. The separated aqueous layer was extracted with diethyl ether. The diethyl ether liquid fractions were pooled and dried to yield the crude, named product, 2.07 g, m.p. 128°-130° C. Recrystallization from a mixture of methylene chloride and Skellysolve® B gave product weighing 1.56 g, m.p. 129°-130.5° C. The elemental analysis was as follows:

후처리

  1. customwas placed in a refrigerator overnight
  2. customUpon removal from the refrigerator
  3. customthe bulk of the solvent was removed on a rotary evaporator
  4. extractionThe separated aqueous layer was extracted with diethyl ether
  5. customdried
  6. customto yield the crude
  7. customRecrystallization
  8. additionfrom a mixture of methylene chloride and Skellysolve® B
  9. customgave product

출처 및 근거

ORD 기록
ord-a3d42107dd764f93a5e1875e51fecd9a
출처 데이터셋
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04346101

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