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

HRID 1372681

反応式

HRID 1372681 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4c7368b2558a4b6f8b6eb27100b196f9
出典データセット
uspto-grants-2007_01
特許番号
US07157487B2

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