Hydrochloric Acid → HCID 59436515、化合物

HRID 46284ノート

反応式

HRID 46284 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH:28][C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17].Cl>CN(C=O)C>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH:28][C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[O:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])#[N:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 110953292-Bromo-6-methylphenolHCID 580423023-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

生成物 1

HCID 59436515HCID 59436515、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-bromo-6-methylphenol (6.0 mmol, 1120 mg) and K2CO3 (10.5 mmol, 1450 mg) in DMF (15.0 mL) was added 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 65, 4.5 mmol, 1280 mg). The reaction mixture was heated at 80° C. After stirring for overnight at 80° C., the reaction was cooled to room temperature and poured into 1 N aqueous HCl (100 mL) to precipitate which was filtered to obtain solid. The solid was washed with water (100 mL) and heptane (100 mL) and the solid was dried under vacuum to furnish the title compound. LCMS Rt=3.05 minutes MS m/z 451 [M(79Br)H]+, 453 [M(81Br)H]+ 1HNMR (d6-DMSO): δ 2.17 (s, 3H), 6.70 (d, 1H), 7.25-7.31 (m, 1H), 7.44-7.48 (m, 1H), 7.64-7.69 (m, 1H), 8.01 (dd, 1H), 8.34 (d, 1H), 8.52 (s, 1H).

後処理

  1. temperaturethe reaction was cooled to room temperature
  2. customto precipitate which
  3. filtrationwas filtered
  4. customto obtain solid
  5. washThe solid was washed with water (100 mL) and heptane (100 mL)
  6. customthe solid was dried under vacuum

出典と根拠

ORDレコード
ord-275dae610a674b7b969fc9cc22e97dd5
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

反応ノート

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