Triethylamine → 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724966ノート

反応式

HRID 724966 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19]O)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.S(Cl)([Cl:25])=O.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][Cl:25])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 10615550HCID 10615550、化合物

生成物 1

HCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one収率 94.5%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

The 2-chloro-5,11-dihydro-11-ethyl-8-hydroxymethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.52 g, 1.6 mmol) was dissolved in chloroform (10 mL) and treated with thionyl chloride (0.12 mL, 1.6 mmol) followed by triethylamine (0.23 mL, 1.6 mmol). After 0.5 hours stirring the mixture was made alkaline with 15% aqueous sodium hydroxide, diluted with brine (10 mL) and the organic layer was separated. The aqueous layer was then extracted with dichloromethane (2×20 mL). The combined organics were dried over sodium sulfate, filtered, concentrated and the residue was purified by flash chromatography (gradient hexanes to 1:1 hexanes/ethyl acetate) to give the title compound (0.51 g, 93%), m.p. 133°-134° C.

後処理

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was then extracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (gradient hexanes to 1:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-74783ae67d934ed89557648205037a90
出典データセット
uspto-grants-1998_01
特許番号
US05705499

反応ノート

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