反応 #9680

反応方程式

ammonium hydroxide

N-(4-iodophenyl)-N′-(4-methylphenyl) thiourea

bromine

sulphurous acid

→

N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine

収率 97.0%

溶媒

chloroform

chloroform

chloroform

反応条件

後処理

1. 1
   温度heated at 50° C. for 5 minutes
2. 2
   温度to cool
3. 3
   workup.DISSOLUTIONto dissolve the precipitate
4. 4
   その他The layers was separated
5. 5
   洗浄the organic layer was washed with water and brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

A suspension of N-(4-iodophenyl)-N′-(4-methylphenyl) thiourea (0.62 g, 4.68 mmol) in chloroform (23 mL) was treated with a solution of bromine (2.65 g, 16.59 mmol) in chloroform (1 mL). The reaction mixture was stirred at rt for 5 minutes and then heated at 50° C. for 5 minutes. Then the reaction mixture was allowed to cool, and was treated with sulphurous acid until the orange color disappeared. The reaction mixture was neutralized by treatment with conc. ammonium hydroxide. More chloroform was then added to dissolve the precipitate. The layers was separated, and the organic layer was washed with water and brine, dried over sodium sulfate, filtered and, concentrated to give N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine (0.6 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ 2.36 (s, 3H), 7.12 (m, 1H), 7.48 (d, 1H), 7.60 (m, 3H), 7.65 (m, 2H), 10.50 (s, 1H).

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