Dimethylformamide → 5-Amino-3-[(dimethylaminomethylidene)amino]-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole

HRID 1289777ノート

反応式

HRID 1289777 の反応式
[NH2:1][C:2]1[N:6]=[C:5]([NH2:7])[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=1.[CH3:12][N:13]([CH3:16])[CH:14]=O.C(N(CC)CC)C.C(Cl)(=O)C1C=CC=CC=1>O>[NH2:7][C:5]1[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=[C:2]([N:1]=[CH:12][N:13]([CH3:16])[CH3:14])[N:6]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10725863HCID 10725863、化合物

生成物 1

HCID 867525445-Amino-3-[(dimethylaminomethylidene)amino]-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole収率 27%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of the compound (1.00 g) obtained in Example 31, dimethylformamide (25 ml) and triethylamine (1.0 ml, 7.2 mmol) was cooled to 0° C. and benzoyl chloride (0.70 ml) was gradually added dropwise thereto. The mixture was stirred at 0° C.-room temperature for 4.5 hours and the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. After the concentration, silica gel column chromatography (chloroform-methanol) and recrystallization from chloroform-methanol gave 350 mg of pale-yellow crystals (yield 27%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. concentrationAfter the concentration, silica gel column chromatography (chloroform-methanol) and recrystallization from chloroform-methanol

出典と根拠

ORDレコード
ord-e1cb432d9a5243da96f4623583cd1305
出典データセット
uspto-grants-1998_05
特許番号
US05750545

反応ノート

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