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

HRID 638015ノート

反応式

HRID 638015 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31347Sulfolane溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-9038774b2a304656a8c8aa2a6ef8dee4
出典データセット
uspto-grants-1985_12
特許番号
US04559404

反応ノート

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