Ammonium thiocyanate → 2-Amino-6-(4-fluorophenoxy)benzothiazole

HRID 359777

반응식

HRID 359777 반응식
BrBr.[F:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[S-:18][C:19]#[N:20].[NH4+]>C(O)(=O)C>[NH2:20][C:19]1[S:18][C:14]2[CH:15]=[C:9]([O:8][C:7]3[CH:16]=[CH:17][C:4]([F:3])=[CH:5][CH:6]=3)[CH:10]=[CH:11][C:12]=2[N:13]=1

참가 물질

5

반응물 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 147633Benzenamine, 4-(4-fluorophenoxy)-

생성물 1

HCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazole수율 81.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

13 ml of acetic acid containing 6.5 ml of bromine were added dropwise at 13 to 15° C. to a solution of 25.6 g of 4-(4-fluorophenoxy)aniline and 19.2 g of ammonium thiocyanate in 185 ml of acetic acid. After completion of the addition, the mixture was stirred at room temperature for 1 hour and then the solvent was distilled off under reduced pressure. The residue was mixed with 300 ml of ethyl acetate and 200 ml of water, and the mixture was neutralized by adding powered potassium carbonate. The ethyl acetate layer was then separated and dried over anhydrous magnesium sulfate, and then the residue was concentrated by evaporation under reduced pressure. The crystalline residue was washed with diisopropyl ether to afford 26.7 g of the title compound, melting at 126-128° C.

후처리

  1. additionAfter completion of the addition
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was mixed with 300 ml of ethyl acetate and 200 ml of water
  4. additionby adding powered potassium carbonate
  5. customThe ethyl acetate layer was then separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthe residue was concentrated by evaporation under reduced pressure
  8. washThe crystalline residue was washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-3bfff5e2471a4e43906f9a62b6d887a3
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05002942

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