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

HRID 9127

반응식

HRID 9127 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazole수율 103.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39cabe140ee74440b053a8e259355b3d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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