Ammonia → 6-Bromo-1,3-benzothiazole

HRID 1477395ノート

反応式

HRID 1477395 の反応式
N([O-])=O.[Na+].N[C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1.N.[BrH:16]>O.Cl.[Cu]Br>[Br:16][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1

参加物

8

反応物 4

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 682886-AminobenzothiazoleHCID 23668193Sodium Nitrite

生成物 1

HCID 27951716-Bromo-1,3-benzothiazole

試薬・触媒・溶媒 3

HCID 24593copper(I) bromide触媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

実験手順

A solution of sodium nitrite (0.147 g, 2.1 mmol) in water (1.0 mL) was slowly added to a suspension of 6-aminobenzothiazole (0.30 g, 2.0 mmol) in HBr (48% in water, 3 mL) at 0° C. and then the mixture was stirred at room temperature for 30 min. The formed solution was then slowly added to a solution of copper (I) bromide (0.435 g, 3.0 mmol) in HCl (conc., 5 mL) at 0° C. After the addition, the mixture was stirred at 60° C. for 1.5 h. Cooled down, and the reaction mixture was basified with excess ammonia and extracted with diethyl ether. The combined extract was washed with water, brine, dried and concentrated. The 6-bromobenzothiazole (0.26 g) was obtained by Combiflash and then converted to the final compound using procedures analogous to those for example 1, MS(ESI): (M+H)+=413.1.

後処理

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 60° C. for 1.5 h
  3. temperatureCooled down
  4. extractionextracted with diethyl ether
  5. extractionThe combined extract
  6. washwas washed with water, brine
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4815b0beb11e4f02ade81403c04ca13d
出典データセット
uspto-grants-2016_08
特許番号
US09403775B2

反応ノート

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