Pyridine → HCID 21062529、化合物

HRID 1242274

反応式

HRID 1242274 の反応式
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[OH:12][CH2:13][CH:14]1[CH2:18][O:17][C:16](=[S:19])[NH:15]1.N1C=CC=CC=1>C1COCC1>[S:19]=[C:16]1[NH:15][CH:14]([CH2:13][O:12][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=2)[CH2:18][O:17]1

参加物

5

反応物 3

HCID 1049PyridineHCID 110520284-Vinylbenzoyl chlorideHCID 21939074HCID 21939074、化合物

生成物 1

HCID 21062529HCID 21062529、化合物収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 4-vinylbenzoyl chloride (21.0 g, 126 mmol) in dry THF (50 mL) was added to a solution of 4-hydroxymethyl-1,3-oxazolidine-2-thione (14.0 g, 105 mmol) in dry THF (250 mL) and pyridine (10.2 mL, 126 mmol) at 0° C. After 12 hours of stirring at room temperature, pyridine hydrochloride was filtered off, and the solvent was evaporated out in vacuo. The residue was purified by silica gel column chromatography eluted with ethyl acetate/acetone (1/1=v/v), followed by recrystallization from a mixed solvent [n-hexane/ethyl acetate (3/1=v/v)] to afford 4-vinylbenzoic acid 2-thioxo-oxazolidin-4-ylmethyl ester as a colorless solid. Yield 73% (24.1 g, 91.5 mmol). 1H NMR (DMSO-d6): δ=4.25–4.77 (5H, >CH—, —CH2—O(CO)—, and —(SC)O—CH2—), 5.45 (d, J=10.8 Hz, 1H, —CH═CH2), 6.03 (d, J=17.8 Hz, 1H, —CH═CH2), 6.84 (dd, J=11.3 and 17.7 Hz, 1H, —CH═CH2), 7.64 (d, J=8.1 Hz, 2H, —C6H4—), 8.01 (d. J=8.1 Hz, 2H, —C6H4—), 10.3 (broad s, 1H, —NH—) ppm. 13C NMR (DMSO-d6): δ=55.0 (CO—CH2—CH<), 65.1 (>CH—), 71.8 (—CH2—O(CO)—), 117.7 (—CH═CH2), 126.5, 128.6, 130.1 (—C6H4—), 136.0 (—CH═CH2), 142.2 (—C6H4—), 165.6 (—O(CO)—C6H4—), 189.3 (>C═S) ppm. IR (KBr): 3185, 1712 (—OCOPh), 1504 (C═S), 1280, 1180, 1110, 971 cm−1.

後処理

  1. filtrationpyridine hydrochloride was filtered off
  2. customthe solvent was evaporated out in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluted with ethyl acetate/acetone (1/1=v/v)
  5. customfollowed by recrystallization from a mixed solvent [n-hexane/ethyl acetate (3/1=v/v)]

出典と根拠

ORDレコード
ord-e294491d536149cc9dabcbaa57e13a54
出典データセット
uspto-grants-2006_10
特許番号
US07115705B2

関連ノート

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