Triethylamine → HCID 19600873、化合物

HRID 609893ノート

反応式

HRID 609893 の反応式
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:17]2[NH:21][CH2:20][CH2:19][S:18]2)[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>O1CCCC1>[C:13]([C:10]1[CH:9]=[C:8]([CH:17]2[N:21]([C:29](=[O:32])[CH:30]=[CH2:31])[CH2:20][CH2:19][S:18]2)[CH:7]=[C:6]([C:2]([CH3:3])([CH3:4])[CH3:5])[C:11]=1[OH:12])([CH3:14])([CH3:15])[CH3:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 19600882HCID 19600882、化合物

生成物 1

HCID 19600873HCID 19600873、化合物収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazolidine hydrochloride (1.65 g) obtained in Reference Example 61 in tetrahydrofuran (20 ml) was added triethylamine (1.52 g), and acryloyl chloride (0.63 g) was added thereto at 0° C. The mixture was stirred at that temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into ice-water; and the product was extracted with chloroform. The organic layer was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate, and brine, then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2) to afford 0.93 g (54%) of the title compound as colorless crystals. mp 147-149° C. NMR (CDCl3) (200 MHz) δ: 1.40 (18H, s), 3.0-3.2 (2H, m), 3.8-4.0 (1H, m), 4.2-4.5 (1H, m), 5.20 (1H, brs), 5.5-5.8 (1H, m), 5.9-6.6 (3H, m), 6.98 (2H, brs)

後処理

  1. additionwas added
  2. customat 0° C
  3. customAfter completion of the reaction
  4. extractionand the product was extracted with chloroform
  5. washThe organic layer was washed successively with 1N hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and brine, then dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2)

出典と根拠

ORDレコード
ord-fdb23ceb162e4ebe81df0fd97393c1bc
出典データセット
uspto-grants-1999_12
特許番号
US05998452

反応ノート

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