Methyl chloroformate → Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate

HRID 1667611ノート

反応式

HRID 1667611 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([NH:1][C:17](=[O:18])[O:19][CH3:20])[CH:3]=[CH:4][C:5]=1[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:8]

参加物

4

反応物 2

HCID 6586Methyl chloroformateHCID 574482075-Amino-2-(isopropylsulfonyl)benzonitrile

生成物 1

HCID 57448208Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate収率 88%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To 15C (450 mg, 2 mmol) in pyridine (10 mL) at 0° C. was added methyl chloroformate (0.8 mL, 10 mmol). The reaction was stirred at 0° C. for 20 min, then warmed to rt for 2 h. The reaction was concentrated, then diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes) to provide 15D (490 mg, 88%). LC-MS: 283.35 (M+H)+.

後処理

  1. temperaturewarmed to rt for 2 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-8b6db5b81d474600a0ed62124ad27042
出典データセット
uspto-grants-2011_10
特許番号
US08044242B2

反応ノート

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