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

HRID 1788288노트

반응식

HRID 1788288 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
100 °C

실험 절차

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)+].

후처리

  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

출처 및 근거

ORD 기록
ord-aa810b331fbb4e18a986c0027bc5c8c1
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511146B2

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