Benzenepropanoyl chloride → 3-phenyl-N-(2-phenyl-1,3-benzoxazol-5-yl)propanamide

HRID 1896746

反応式

HRID 1896746 の反応式
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:17]1([CH2:23][CH2:24][C:25]([NH:16][C:13]2[CH:14]=[CH:15][C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=2)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 7210592-Phenyl-1,3-benzoxazol-5-amine

生成物 1

HCID 9760393-phenyl-N-(2-phenyl-1,3-benzoxazol-5-yl)propanamide収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-phenylbenzo[d]oxazol-5-amine (50 mg, 0.24 mmol) in dichloromethane (2 mL) at room temperature was added 3-phenylpropanoyl chloride (44.1 mg, 0.26 mmol) followed immediately by diisopropylethylamine (82 μL, 0.48 mmol). The resulting mixture was stirred at room temperature for 16 h. Dichloromethane was added and the organic layer was washed with saturated aqueous Na2CO3. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was dissolved in methanol, passed through an acidic scavenger column (silica-based quaternary amine SPE-AX from Biotage®) and then evaporated to afford 61.1 mg (75%) of the title compound (LCMS RT=6.45 min, MH+ 343.2)

後処理

  1. washthe organic layer was washed with saturated aqueous Na2CO3
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. dissolutionThe resulting solid was dissolved in methanol
  5. customevaporated

出典と根拠

ORDレコード
ord-03838efeabaa4d9fb9e6abfc63b631db
出典データセット
uspto-grants-2013_08
特許番号
US08518980B2

関連ノート

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