Water → 3-Chloro-4-cyano-2-methylphenylacetamide

HRID 15183

반응식

HRID 15183 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([CH3:12])[C:3]=1[Cl:13].[Cu](C#N)[C:15]#[N:16].O>CN(C=O)C>[Cl:13][C:3]1[C:4]([CH3:12])=[C:5]([CH2:8][C:9]([NH2:11])=[O:10])[CH:6]=[CH:7][C:2]=1[C:15]#[N:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 684571414-Bromo-3-chloro-2-methylphenylacetamideHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 684580283-Chloro-4-cyano-2-methylphenylacetamide수율 67%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A suspension of bromide 1B (2.7 g, 10.3 mmol) and copper cyanide (0.92 g, 10.3 mmol) in DMF (30 mL) was heated to 150° C. for 4 h. The suspension was cooled, poured into water with stirring, and the solid was filtered and dried to give 1.44 g (67%) of the desired nitrile. 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 2.29 (s, 3H), 7.72 (d, J=8.8, 1H), 7.75 (d, J=8.2, 1H), 9.73 (s, 1H); 13C NMR (DMSO-d6) δ 15.3, 23.5, 107.7, 116.5, 123.0, 130.1, 131.5, 135.7, 142.3, 168.8; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.23 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.13 min retention time (95%); MS (ES) m/z 209 [M+H]+.

후처리

  1. temperatureThe suspension was cooled
  2. filtrationthe solid was filtered
  3. customdried

출처 및 근거

ORD 기록
ord-cf2a4d3c6c984fa3b7bfa4b7474a44e2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732480B2

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