Ammonium Hydroxide → 4-Trifluoromethyl-thiazole-2-carboxylic acid amide

HRID 388705ノート

反応式

HRID 388705 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8](O)=[O:9])[S:6][CH:7]=1.C1N=C[N:15](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>C1COCC1>[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8]([NH2:15])=[O:9])[S:6][CH:7]=1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 186730104-(Trifluoromethyl)thiazole-2-carboxylic acid

生成物 1

HCID 595334044-Trifluoromethyl-thiazole-2-carboxylic acid amide収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-trifluoromethyl-thiazole-2-carboxylic acid (50 g, 1 eq.) in anhydrous THF (480 mL) was added carbodiimidazole (45.2 g, 1.1 eq.) portionwise under nitrogen in an ice/water bath (about 5° C.). The reaction mixture was stirred at room temperature for 16 hrs. NH4OH (25% in H2O; 1.930 mL) was added. The solution was stirred for 4 hrs, and then partitioned in DCM (500 mL) and H2O (500 mL). Aqueous layer was further extracted with DCM (500 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to yield compound 285a as an orange solid in 72% yield. MS (ESI, EI+) m/z=197 (MH+).

後処理

  1. stirringThe solution was stirred for 4 hrs
  2. custompartitioned in DCM (500 mL)
  3. extractionAqueous layer was further extracted with DCM (500 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8b5ca17d601a468db167d38fc622bcdf
出典データセット
uspto-grants-2013_02
特許番号
US08377962B2

反応ノート

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