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

HRID 250013

반응식

HRID 250013 반응식
[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

참가 물질

6

반응물 4

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanate2회HCID 7373634-(Difluoromethoxy)aniline

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c8c3eff73804232af6b26a08d8f76c1
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863291B2

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