Benzonitrile, m-chloro- → HCID 67070903, 화합물

HRID 732132

반응식

HRID 732132 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 67070903HCID 67070903, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-1fcec38ba4fe4e71a2b688ccd8f544c4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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