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Triethylamine → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1436467
ノート
印刷プレビュー

反応式

HRID 1436467 の反応式
C(N(CC)CC)C.[OH:8][CH2:9][C:10]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1)([CH3:12])[CH3:11].Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.O.C(OCC)(=O)C>O1CCCC1>[CH3:11][C:10]1([CH3:12])[CH2:9][O:8][C:28](=[O:30])[N:13]1[C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22728543Water ethylacetateHCID 866186224-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

生成物 1

HCID 689019664-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile収率 36%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of triethylamine (0.42 mL, 3 mmol) and 4-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (0.75 g, 2.71 mmol), prepared in the previous step, in dry tetrahydrofuran (10 mL) was added triphosgene (0.83 g, 2.8 mmol) at room temperature. After 16 h, the mixture was poured into water/ethyl acetate. The organic layer was washed with water, dried (anhydrous sodium sulfate) and evaporated. The product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.29 g, 36%) as a white powder. HRMS: calcd for C14H14N4O2S [M+H]+, 303.09102; found (ESI, [M+H]+), 303.0914; ANLC 99.6% at 210-370 nm, 9.0 min; 99.5% at 260 nm, 9.0 min, the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

後処理

  1. washThe organic layer was washed with water
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customevaporated
  4. customThe product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4)

出典と根拠

ORDレコード
ord-9271670c15374ba7b85ed0ac077ec0ab
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07618990B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート