Chloroacetic Acid → 2-(Chloromethyl)benzothiazole

HRID 7086

반응식

HRID 7086 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Cl:9][CH2:10][C:11](O)=[O:12].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:9][CH2:10][C:11]1[O:12][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1.[Cl:9][CH2:10][C:11]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

참가 물질

6

반응물 3

HCID 300Chloroacetic AcidHCID 87132-AminothiophenolHCID 11430Potassium Carbonate

생성물 2

HCID 3049782-(Chloromethyl)benzothiazoleHCID 20619892-(Chloromethyl)-1,3-benzoxazole

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

Using literature procedures (Addison, A. W.; Nageswara Rao, T.; Wahlgren, C. G. J. Heterocyclic Chem. 1983, 20, 1481–1484) a substituted 2-aminophenol (or a 2-aminothiophenol (5 mmol)) was mixed with chloroacetic acid (940 mg, 10 mmol) in polyphosphoric acid (5 mL), and the viscous mixture was then heated to 120° C. for 3 hours. The reaction was then cooled, and diluted with water (˜20 mL) and then neutralized with potassium carbonate to pH˜7. The mixture was then extracted with ethyl acetate, and the combined organic fractions were then dried over MgSO4 and concentrated. The residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes) to afford the desired 2-chloromethylbenzoxazole (or 2-chloromethylbenzothiazole).

후처리

  1. temperatureThe reaction was then cooled
  2. extractionThe mixture was then extracted with ethyl acetate
  3. dry with materialthe combined organic fractions were then dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-1b495aa703b04744bb5cf439eed00b5d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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