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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
ノート
印刷プレビュー

反応式

HRID 67688 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-a3d42107dd764f93a5e1875e51fecd9a
出典データセット
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04346101

反応ノート

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