O-Phenylenediamine → 2-[(4-chlorophenoxy)methyl]-1H-1,3-benzodiazole

HRID 537299

反応式

HRID 537299 の反応式
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16](O)=O)=[CH:12][CH:11]=1>Cl>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:16]=1[CH2:15][O:14][C:13]1[CH:19]=[CH:20][C:10]([Cl:9])=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 7243O-PhenylenediamineHCID 26229(4-Chlorophenoxy)acetic acid

生成物 1

HCID 3939882-[(4-chlorophenoxy)methyl]-1H-1,3-benzodiazole収率 68%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A suspension of phenylene diamine (10.8 g, 0.1 mol) and 4-chlorophenoxyacetic acid (18.66 g, 0.1 mol) in 4M HCl (150 mL) was refluxed overnight under Ar. The reaction mixture was then cooled in an ice bath. The solid was collected and washed with H2O (150 mL). To the solid was added MeOH (100 mL), CH2Cl2 (400 mL) and 20% aqueous NaOH (300 mL). After stirring for 30 min, the organic phase was separated, filtered through phase separation filter paper, and concentrated in vacuo to give a solid. This solid was triturated with hexanes (150 mL), collected, washed with hexanes (100 mL), and dried to give 17.5 g (68%) of 52 as a pink solid. The HPLC analysis showed a purity of 100%. 1H NMR (60 MHz, d6-DMSO): δ 11.5 (br s, 1H), 6.9-7.5 (m, 8H), 5.3 (s, 2H).

後処理

  1. temperaturewas refluxed overnight under Ar
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. customThe solid was collected
  4. washwashed with H2O (150 mL)
  5. additionTo the solid was added MeOH (100 mL), CH2Cl2 (400 mL) and 20% aqueous NaOH (300 mL)
  6. customthe organic phase was separated
  7. filtrationfiltered through phase separation
  8. filtrationfilter paper
  9. concentrationconcentrated in vacuo
  10. customto give a solid
  11. customThis solid was triturated with hexanes (150 mL)
  12. customcollected
  13. washwashed with hexanes (100 mL)
  14. customdried

出典と根拠

ORDレコード
ord-c2602c00435c4cffb9057476186bbdf8
出典データセット
uspto-grants-2014_10
特許番号
US08859780B2

関連ノート

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