Methanesulfonic Acid → Tilomisole

HRID 478052

反応式

HRID 478052 の反応式
Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[N:16]3[C:12](=[N:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)[S:11][CH:10]2[CH2:21][C:22]([OH:24])=[O:23])=[CH:5][CH:4]=1.CS(O)(=O)=O.C(OCC)(=O)C.C(O)(=O)C.C([O-])(=O)C.C(O)(=O)C>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:16]3[C:12](=[N:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=43)[S:11][C:10]=2[CH2:21][C:22]([OH:24])=[O:23])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 6395Methanesulfonic AcidHCID 122818063-(p-Chlorophenyl)-2,3,-dihydro-3-hydroxythiazolo[3,2-a]benzimidazol-2-acetic acid, hydrobromideHCID 21252148Acetate acetic acidHCID 22609514Ethyl acetate acetate

生成物 1

HCID 42747Tilomisole収率 96.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 100 g of 3-(p-Chlorophenyl)-2,3,-dihydro-3-hydroxythiazolo[3,2-a]benzimidazol-2-acetic acid, hydrobromide and 200 ml of methanesulfonic acid was stirred overnight in a 500 ml round bottom flask. Thin layer chromatography on silica plates (solvent ethyl acetate/acetic acid) indicated rapid formation of an intermediate. After 20 hours at room temperature thin layer chromatography (silica plates, ethyl) acetate/acetic acid) showed the presence of a single component. The mixture was poured into water and the resulting crystals removed by filtration. The crystalline product was suspended in 5 volumes of hot water for 1/2 hour, filtered and the procedure repeated. After a final aqueous wash the material was dried in vacuo to yield the title compound (75 g, 91%) m.p. 242°-3° C.

後処理

  1. customthe resulting crystals removed by filtration
  2. waitThe crystalline product was suspended in 5 volumes of hot water for 1/2 hour
  3. filtrationfiltered
  4. washAfter a final aqueous wash the material
  5. customwas dried in vacuo

出典と根拠

ORDレコード
ord-38716f1ad7844c2bb4923765ba2ae21d
出典データセット
uspto-grants-1989_12
特許番号
US04889936

関連ノート

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