Sodium Carbonate → N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amine

HRID 659134ノート

反応式

HRID 659134 の反応式
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][C:10]#[CH:11])=[O:6].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH3:4].[C:12]1([CH:8]([NH:7][C:5]2[O:6][CH2:2][CH2:3][N:4]=2)[CH2:9][C:10]#[CH:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 574298141-(2-Chloroethyl)-3-(1-phenylbut-3-ynyl)urea2 回

生成物 2

HCID 222Ammonia収率 4%HCID 44480251N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amine収率 63.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 200 mg of 1-(2-chloroethyl)-3-(1-phenylbut-3-ynyl)urea (Formula 18) in 5 mL of water was heated at 100° C. for 2.5 hours. The reaction mixture was cooled to room temperature. Then, a saturated solution of sodium carbonate was added until the pH of the solution was greater than 8. The mixture was extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (4% 7N NH3 in CH3OH/CH2Cl2) gave 54 mg of N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amine (Formula 19) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.98-2.00 (m, 1H), 2.66-2.84 (m, 2H), 3.68-3.76 (m, 2H), 4.20-4.26 (m, 2H), 4.83-4.87 (m, 1H), 7.25-7.39 (m, 5H).

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washCombined ethyl acetate was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae5544cfdd324a8289281b392ef15004
出典データセット
uspto-grants-2011_12
特許番号
US08080570B2

反応ノート

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