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

HRID 49136

반응식

HRID 49136 반응식
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]

참가 물질

7

반응물 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)

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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%).

후처리

  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.

출처 및 근거

ORD 기록
ord-8ac3bf7b1da540dd963f8322954ff904
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706717B2

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