Bromine → 2-Amino-6-(4-fluorophenoxy)benzothiazole

HRID 9127

反応式

HRID 9127 の反応式
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:16]([S-:18])#[N:17].[K+].BrBr>C(O)(=O)C>[NH2:17][C:16]1[S:18][C:12]2[CH:13]=[C:7]([O:6][C:5]3[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=3)[CH:8]=[CH:9][C:10]=2[N:11]=1

参加物

5

反応物 3

HCID 24408BromineHCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 516872Potassium thiocyanate

生成物 1

HCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazole収率 103.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of 4-(4′-fluorophenoxy)aniline (0.305 g, 1.50 mmol) and KSCN (0.29 g, 3.00 mmol, 2.0 eq) in 3 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.077 mL, 1.50 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 2 hours. The precipitate was filtered off and washed with Et2O. The mother liquid from the filtration was concentrated, and the residue was combined with the precipitate. The obtained solid was neutralized with saturated sodium carbonate solution, and a new precipitate was formed. It was filtered off, washed with water, and dried under vacuum to give the desired compound 0.403 g (90%). LC/MS 261.2 (M+1); LC retention time 2.44 min.

後処理

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O
  3. filtrationThe mother liquid from the filtration
  4. concentrationwas concentrated
  5. customa new precipitate was formed
  6. filtrationIt was filtered off
  7. washwashed with water
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-39cabe140ee74440b053a8e259355b3d
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

関連ノート

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