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

HRID 1788288

Reaction equation

HRID 1788288 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

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)+].

Workup

  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

Sources & evidence

ORD record
ord-aa810b331fbb4e18a986c0027bc5c8c1
Source dataset
uspto-grants-2009_03
Patent number
US07511146B2

Linked notes

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