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Chlorosulfonyl isocyanate → Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate

HRID 1591837
ノート
印刷プレビュー

反応式

HRID 1591837 の反応式
[CH2:1]([S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4])[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O>O1CCCC1>[C:30]([C:15]1[N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:13]([C:10]2[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:12][CH:11]=2)=[CH:17][CH:16]=1)#[N:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 70918Chlorosulfonyl isocyanateHCID 69412284tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate

生成物 1

HCID 16051190Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate (3.0 g, 8.58 mmol) was dissolved in tetrahydrofuran (85 mL) and cooled to −78° C., followed by the slow addition of chlorosulfonyl isocyanate. After tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed, dimethyl formamide (6.86 mL) was added and the solution allowed to warm to room temperature. After 2 hours, the mixture was cooled and partitioned between water and diethyl ether. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (1.84 g, 57%). The title compound was used immediately in the next step.

後処理

  1. customAfter tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed
  2. additiondimethyl formamide (6.86 mL) was added
  3. temperatureto warm to room temperature
  4. temperaturethe mixture was cooled
  5. custompartitioned between water and diethyl ether
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3)

出典と根拠

ORDレコード
ord-7fee40175bcb41cb9cc38f0cffe36a89
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07291643B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート