Hydrochloric Acid → Venom

HRID 1397182ノート

反応式

HRID 1397182 の反応式
[H-].[Na+].[CH3:3][N:4]1CN(C)[CH2:7][NH:6][C:5]1=[N:11][N+:12]([O-:14])=[O:13].O(C[CH:24]1[CH2:28][CH2:27][O:26][CH2:25]1)S(C(F)(F)F)(=O)=O.Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[O:26]1[CH2:27][CH2:28][CH:24]([CH2:7][NH:6][C:5]([NH:4][CH3:3])=[N:11][N+:12]([O-:14])=[O:13])[CH2:25]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 216645293-Tetrahydrofuranylmethyl triflateHCID 135476318N-(1,5-dimethyl-1,3,5-triazinan-2-ylidene)nitramide

生成物 1

HCID 135779803Venom収率 53.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture comprising 10.0 g of (tetrahydro-3-furanyl)methanol, 29.5 g of trifluoromethanesulfonic anhydride, 10.0 g of pyridine and 200 ml of dichloromethane was stirred for an hour at room temperature. Water was poured into the reaction solution to separate the organic layer, which was washed with 1 N hydrochloric acid, water and a saturated saline solution, dried, and concentrated to obtain 20 g of 3-tetrahydro-furanylmethyl triflate. 3.25 g of 60% sodium hydride were added to 12.5 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine and 60 ml of DMF at room temperature, followed by stirring for an hour. 20.0 g of the 3-tetrahydrofuranylmethyl triflate were added thereto, and the mixture was stirred at 50° C. for 2 hours. After cooling the mixture to room temperature, 50 ml of 2N hydrochloric acid were added thereto, followed by stirring at 50° C. for 2 hours. The resultant mixture was neutralized with sodium bicarbonate and extracted with dichloromethane, and the extract was dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (eluent: 1:1 ratio of ethyl acetate/hexane) to obtain 7.8 g of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran).

後処理

  1. stirringthe mixture was stirred at 50° C. for 2 hours
  2. stirringby stirring at 50° C. for 2 hours
  3. extractionextracted with dichloromethane
  4. customthe extract was dried
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (eluent: 1:1 ratio of ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-10c5fa4888ff4d7eb1f603e110357fca
出典データセット
uspto-grants-2014_12
特許番号
US08901154B2

反応ノート

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