Bromine → Methyl 5-amino-1,2,4-thiadiazole-3-carboxylate

HRID 543827ノート

反応式

HRID 543827 の反応式
Br.[CH2:2]([O:4][C:5]([C:7]([NH2:9])=[NH:8])=[O:6])C.[Na].BrBr.[S-:13][C:14]#[N:15].[K+]>CO>[NH2:15][C:14]1[S:13][N:9]=[C:7]([C:5]([O:4][CH3:2])=[O:6])[N:8]=1

参加物

6

反応物 4

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 5360545Sodium2 回HCID 233168511-Ethoxycarbonylformamidine hydrobromide

生成物 1

HCID 13577102Methyl 5-amino-1,2,4-thiadiazole-3-carboxylate収率 67.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒4 回

反応条件

温度
0 °C

実験手順

To a solution of 1-ethoxycarbonylformamidine. hydrobromide (16.6 g) in absolute methanol (84 ml) was added a solution of sodium (1.93 g) in absolute methanol (42 ml) at 0° C. To the mixture were added alternately bromine (12.8 g) and a solution of sodium (1.93 g) in absolute methanol (42 ml) at 0° C. and then to the suspension was added potassium thiocyanate (8.1 g) in absolute methanol (100 ml). The reaction mixture was stirred for an hour at 0° C. and for an additional 6 hours at ambient temperature. The mixture was filtered through cellulose powder and the filtrate was evaporated to dryness. The residue was dissolved in a mixture of ethyl acetate and water, and then the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was triturated with diethyl ether to give the title compound (9.0 g), mp. 202° to 205° C.

後処理

  1. filtrationThe mixture was filtered through cellulose powder
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  4. customthe ethyl acetate layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-f19dbf6ddf3c47fe9e213240f9191c53
出典データセット
uspto-grants-1984_05
特許番号
US04447429

反応ノート

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