Triethylamine → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

HRID 1867350

反応式

HRID 1867350 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])/[CH:5]=[CH:6]/[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH:20]1[CH2:26][CH2:25][C:24](=[O:27])[NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:6]/[C:7]([N:20]2[CH2:26][CH2:25][C:24](=[O:27])[NH:23][CH2:22][CH2:21]2)=[O:9])[CH:10]=[CH:11][C:12]=1[Cl:13]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 6880273,4-Dichlorocinnamic acidHCID 27372641,4-Diazepan-5-one

生成物 1

HCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one収率 64.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 9.77 g (43.65 mmol) of (E)-3,4-dichlorocinnamic acid in 250 ml of CH2Cl2 was treated at RT with 3 drops of DMF. 4.15 ml (48.02 mmol, 1.1 eq) of oxalyl chloride in 30 ml CH2Cl2 were added dropwise and stirring was continued for 3 h. The solution was evaporated, redissolved in 170 ml of CH2Cl2, cooled (0° C.) and treated with a solution of 4.48 g (39.29 mmol, 0.9 eq) of 2,3,6,7-tetrahydro-(1H)-1,4-diazepin-5(4H)-one and 12.17 ml (87.30 mmol, 2 eq) of triethylamine in 80 ml of CH2Cl2. The reaction was warmed up over night to RT, then partitioned between CH2Cl2/MeOH 9:1 (×3)/ aqueous 10% KHSO4, the organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried over Na2SO4 and evaporated. The residue was dissolved and evaporated with toluene and crystallized with CH2Cl2/Et2O to give 7.99 g (58%) of the title compound as white solid. MS: 312.8 (MH+, 2Cl).

後処理

  1. customThe solution was evaporated
  2. dissolutionredissolved in 170 ml of CH2Cl2
  3. temperatureThe reaction was warmed up over night to RT
  4. custompartitioned between CH2Cl2/MeOH 9:1 (×3)/ aqueous 10% KHSO4
  5. washthe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. dissolutionThe residue was dissolved
  9. customevaporated with toluene
  10. customcrystallized with CH2Cl2/Et2O

出典と根拠

ORDレコード
ord-26b01004002f403a85a04c4e674cf6f2
出典データセット
uspto-grants-2009_12
特許番号
US07632829B2

関連ノート

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