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

HRID 30899

반응식

HRID 30899 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9043f7dd576c4a4bb0909f02be421dbe
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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