Hydrochloric Acid → 3-[(2-Aminothiazol-5-yl)thio]benzoic acid ethyl ester

HRID 49136

反応式

HRID 49136 の反応式
C[O-].[Na+].Cl.[NH2:5][C:6]1[S:7][C:8](Br)=[CH:9][N:10]=1.[C:12]([C:15]1[CH:16]=[C:17]([SH:21])[CH:18]=[CH:19][CH:20]=1)([OH:14])=[O:13].Cl.O1CCO[CH2:25][CH2:24]1>CO>[CH2:24]([O:13][C:12](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21][C:8]2[S:7][C:6]([NH2:5])=[N:10][CH:9]=2)[CH:16]=1)[CH3:25]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 95737Benzoic acid, 3-mercapto-HCID 10942334Sodium MethoxideHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)

生成物 1

HCID 867593833-[(2-Aminothiazol-5-yl)thio]benzoic acid ethyl ester収率 75%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A 4.37 M solution of sodium methoxide in methanol (10 mL, 43.7 mmol) was added dropwise to a stirred suspension of 2-amino-5-bromothiazole hydrochloride (2.16 g, 10 mmol) and 3-carboxythiophenol (1.85 g, 12 mmol) in methanol (75 mL) at 0-5° C. The solution was allowed to warm to rt. for 2 h and a 4 M solution of hydrogen chloride in dioxane (15 mL, 60 mmol) was added. The suspension was stirred at rt. overnight and concentrated. The crude residue was diluted with satd. aqueous sodium bicarbonate solution (50 mL). The precipitated solid was filtered and washed with water (20 mL, 5×) and ether (20 mL, 5×). The solid was filtered and dried in vacuo at 60° C. to obtain the titled compound (1.97 g, 75%).

後処理

  1. concentrationovernight and concentrated
  2. additionThe crude residue was diluted with satd
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (20 mL, 5×) and ether (20 mL, 5×)
  5. filtrationThe solid was filtered
  6. customdried in vacuo at 60° C.

出典と根拠

ORDレコード
ord-8ac3bf7b1da540dd963f8322954ff904
出典データセット
uspto-grants-2004_03
特許番号
US06706717B2

関連ノート

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