Methyl 2-(4-amino-3-chlorophenyl)acetate → Methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetate

HRID 1372681

반응식

HRID 1372681 반응식
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[Cl:24].[NH+]1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=2[N:6]=1

참가 물질

5

반응물 3

HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetateHCID 178593962-Bromo-5-fluorobenzo[d]thiazoleHCID 22033616Pyridinium.p-toluenesulfonate

생성물 1

HCID 58778358Methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetate수율 37.5%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

In xylene (5 ml), 2-bromo-5-fluorobenzothiazole (516 mg, 2.22 mmol), methyl 4-amino-3-chlorophenylacetate (444 mg, 2.22 mmol), and pyridinium•p-toluenesulfonate (PPTS) (168 mg, 0.67 mmol) were heated under reflux for 10 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1, v/v) eluate fractions, methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetate (292 mg, 37%) was obtained as a pale yellow oil.

후처리

  1. temperatureunder reflux for 10 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1

출처 및 근거

ORD 기록
ord-4c7368b2558a4b6f8b6eb27100b196f9
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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