Chloroacetic Acid → 2-(chloromethyl)-5,6-difluoro-1H-1,3-benzodiazole

HRID 1788288

反応式

HRID 1788288 の反応式
[F:1][C:2]1[C:3](N)=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[F:8].[Cl:11][CH2:12][C:13](O)=O.[NH4+:16].[OH-]>Cl>[Cl:11][CH2:12][C:13]1[NH:9][C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[CH:6][C:5]=2[N:16]=1

参加物

5

反応物 3

HCID 300Chloroacetic AcidHCID 14923Ammonium HydroxideHCID 27367533,4-Difluorobenzene-1,2-diamine

生成物 1

HCID 180713122-(chloromethyl)-5,6-difluoro-1H-1,3-benzodiazole

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1 g of 3,4-difluoro-1,2-phenylenediamine (6.94 mmol) and 0.983 g of chloro-acetic acid (10.41 mmol, 1.5 eq) in 13 mL of 4N aqueous HCl was heated to 100° C. for 3 h. The mixture was poured onto ice (10 g), neutralized by the addition of NH4OH and extracted with three 30 mL portions of ethyl acetate. The organic extracts were combined and dried over Na2SO4, filtered and concentrated by rotary evaporation to give 1.28 g of 2-chloromethyl-5,6-difluoro-1H-benzoimidazole as a brown solid. 1H NMR (300 MHz, CDCl3/CD3OD): δ 7.30-7.25 (m, 2H), 4.68 (s, 2H); MS (ESI): Calcd m/z for C8H5ClF2N2.H+=203.1. Found m/z=203.2/205.2 [(M+1)+/(M+3)+].

後処理

  1. additionThe mixture was poured onto ice (10 g)
  2. extractionextracted with three 30 mL portions of ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-aa810b331fbb4e18a986c0027bc5c8c1
出典データセット
uspto-grants-2009_03
特許番号
US07511146B2

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