Benzonitrile, m-chloro- → HCID 67070903、化合物

HRID 732132

反応式

HRID 732132 の反応式
[OH:1][N:2]=[C:3]([Br:5])Br.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CC(=O)OCC>[Br:5][C:3]1[N:11]=[C:10]([C:9]2[CH:12]=[CH:13][CH:14]=[C:7]([Cl:6])[CH:8]=2)[O:1][N:2]=1

参加物

6

反応物 3

HCID 13015Benzonitrile, m-chloro-HCID 516892Sodium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

生成物 1

HCID 67070903HCID 67070903、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Hydroxycarbonimidic dibromide (2.21 g, 10.89 mmol) was added portionwise over 1 h 20 min to a mixture of 3-chlorobenzonitrile (3.00 g, 21.29 mmol) and NaHCO3 (2.9 g, 34.87 mmol) in toluene (3 ml) at 90° C. Stirring was continued for 3 h and then the reaction mixture was cooled to r.t., diluted with EA and washed with water. The organic phase was dried and concentrated. A mixture of 3-chlorobenzonitrile and 3-bromo-5-(3-chlorophenyl)-1,2,4-oxadiazole was obtained after flash chromatography (hex/EA 10:1). 1.0 g of the mixture was dissolved in MeNH2 (4 ml, 8.5 M in EtOH) and heated in a microwave reactor for 30 min at 60° C. The volatiles were removed under reduced pressure and the residue was dissolved in water and extracted with CHCl3. The organic phase was dried and concentrated. Recrystallization from EA gave 137 mg of the title compound. 1H NMR: 3.00 (d, 3 H) 4.35 (bs, 1 H) 7.43 (t, 1 H) 7.50-7.55 (m, 1 H) 7.92 (d, 1 H) 8.03 (s, 1 H)

後処理

  1. washwashed with water
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. additionA mixture of 3-chlorobenzonitrile

出典と根拠

ORDレコード
ord-1fcec38ba4fe4e71a2b688ccd8f544c4
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

関連ノート

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