4-Bromobenzoic acid → 5-Bromo-2-(4-bromophenyl)-1,3-benzothiazole

HRID 1903555노트

반응식

HRID 1903555 반응식
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[C:5]([NH2:10])[CH:4]=1.[Br:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=O)=[CH:14][CH:13]=1.O.CO>S1(CCCC1)(=O)=O>[Br:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]2[S:9][C:6]3[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][C:5]=3[N:10]=2)=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 114644-Bromobenzoic acidHCID 202552762-Amino-4-bromobenzene-1-thiol--hydrogen chloride (1/1)HCID 22242641Methanol--water (1/1)

생성물 1

HCID 135875765-Bromo-2-(4-bromophenyl)-1,3-benzothiazole

시약·촉매·용매 1

HCID 31347Sulfolane용매

반응 조건

온도
70 °C

실험 절차

A mixture of 20 g (0.083 mole) of 4-bromo-2-aminothiophenol hydrochloride and 270 g of deoxygenated polyphosphoric acid was heated at 70° C. for 4 hours. To this mixture was added a solution containing 22 g (0.11 mole) of p-bromobenzoic acid dissolved in 109 g of sulfolane. The reaction mixture was slowly heated to 200° C. and maintained at that temperature for 1 hour. After cooling, the reaction mixture was poured into a 1:1 water-methanol solution to precipitate the product. The light tan precipitate was filtered, washed with dilute ammonium hydroxide, washed with water, and then air dried. The 2-(4-bromophenyl)-5-bromobenzothiazole was recrystallized from toluene to give 24.5 g (80% of theoretical), m.p. 162°-163° C.

후처리

  1. additionTo this mixture was added a solution
  2. temperatureThe reaction mixture was slowly heated to 200° C.
  3. temperaturemaintained at that temperature for 1 hour
  4. temperatureAfter cooling
  5. customto precipitate the product
  6. filtrationThe light tan precipitate was filtered
  7. washwashed with dilute ammonium hydroxide
  8. washwashed with water
  9. customair dried
  10. customThe 2-(4-bromophenyl)-5-bromobenzothiazole was recrystallized from toluene
  11. customto give 24.5 g (80% of theoretical), m.p. 162°-163° C.

출처 및 근거

ORD 기록
ord-107440b7545845ca9d5a7430b8a8b596
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04436886

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