Chloroacetyl chloride → HCID 13365860、化合物

HRID 334516ノート

反応式

HRID 334516 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].C([O-])([O-])=O.[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([NH:7][NH:8][C:21](=[O:22])[CH2:20][Cl:19])=[O:6]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 27359663,5-dichlorobenzohydrazide

生成物 1

HCID 13365860HCID 13365860、化合物収率 93.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 3,5-dichlorobenzohydrazide 5 (0.5 g, 2.4 mmol) and K2CO3 (0.61 g, 4.4 mmol) in acetonitrile (30 mL) was added 2-chloroacetyl chloride (0.41 g, 3.66 mmol) dropwise at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The solid was collected, washed with H2O and ether, and dried to afford 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 92%) which was used for the next step without further purification. A mixture of 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 2.24 mmol) and phosphorous oxychloride (0.51 g, 3.36 mmol) in acetonitrile (20 mL) was stirred under reflux for 16 hours and concentrated. The residue was subjected to flush column chromatography eluting with 10-25% acetone/hexanes to give compound 7 (0.52 g). Yield: 88%.

後処理

  1. customThe solid was collected
  2. washwashed with H2O and ether
  3. customdried

出典と根拠

ORDレコード
ord-bb364b2401db429ab2e07ea7f6e7689b
出典データセット
uspto-grants-2014_11
特許番号
US08883827B2

反応ノート

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