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

HRID 907722

反応式

HRID 907722 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[S:10])=[CH:4][CH:3]=1.BrBr.S(=O)(O)O.[OH-].[NH4+]>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:17]3[CH:16]=[C:15]([CH3:18])[CH:14]=[CH:13][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 1100Sulfurous AcidHCID 14923Ammonium HydroxideHCID 24408BromineHCID 5017958N-(4-iodophenyl)-N'-(4-methylphenyl)thiourea

生成物 1

HCID 21985719N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine収率 97%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒3 回

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).

後処理

  1. temperatureheated at 50° C. for 5 minutes
  2. temperatureto cool
  3. dissolutionto dissolve the precipitate
  4. customThe layers was separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0e636b031ff34a938104351f61128891
出典データセット
uspto-grants-2011_09
特許番号
US08013166B2

関連ノート

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