Ammonium Hydroxide → 6-(Difluoromethoxy)-1,3-benzothiazol-2-amine

HRID 250013

反応式

HRID 250013 の反応式
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[S-:12][C:13]#[N:14].[K+].BrBr.[OH-].[NH4+]>C(O)(=O)C>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]2[N:8]=[C:13]([NH2:14])[S:12][C:6]=2[CH:5]=1

参加物

6

反応物 4

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanate2 回HCID 7373634-(Difluoromethoxy)aniline

生成物 1

HCID 195858986-(Difluoromethoxy)-1,3-benzothiazol-2-amine収率 87.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To 4-(difluoromethoxy)aniline (9.55 g, 60 mmol) in acetic acid (90 mL) was added potassium thiocyanate (KSCN) (12.41 mL, 240 mmol). The mixture was stirred for 20 minutes (KSCN dissolved into solution). To this mixture bromine (3.08 mL, 60.0 mmol) in acetic acid (40 mL) was added dropwise over 20 minutes. The reaction was stirred at room temperature overnight. It was poured into a mixture of 800 ml ice water and 200 ml saturated ammonium hydroxide. The product was extracted with ethyl acetate (5×). The organics were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford 6-(difluoromethoxy)benzo[d]thiazol-2-amine (12.6 g, 52.4 mmol, 87% yield) as a yellow solid.

後処理

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionThe product was extracted with ethyl acetate (5×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8c8c3eff73804232af6b26a08d8f76c1
出典データセット
uspto-grants-2011_01
特許番号
US07863291B2

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