Potassium Carbonate → HCID 68451991、化合物

HRID 2355067ノート

反応式

HRID 2355067 の反応式
Cl.[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH:6]1[CH2:10][NH:9][CH2:8][CH2:7]1.Br[C:16]1[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][C@H:6]1[CH2:7][CH2:8][N:9]([C:16]2[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=2)[CH2:10]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 533885265-Bromo-1,3,4-thiadiazole-2-carbonitrileHCID 53409201HCID 53409201、化合物

生成物 1

HCID 68451991HCID 68451991、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 4-(2-bromophenoxy)pyrrolidine hydrochloride (0.5 g, 1.87 mmol) and 5-bromo-1,3,4-thiadiazole-2-carbonitrile (0.36 g, 1.87 mmol) in DMF (10 mL) was added K2CO3 (0.77 g, 5.61 mmol) under a nitrogen atmosphere. The mixture was stirred at 70° C. for 4 h. After dilution with water, the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and purified by preparative TLC with petroleum:EtOAc (2:1) to give the title compound. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 1H), 7.52 (t, 1H), 7.08 (t, 1H), 6.99 (d, 1H), 5.24 (m, 1H), 3.69-3.93 (m, 4H), 2.33-2.56 (m, 2H).

後処理

  1. extractionAfter dilution with water, the mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. custompurified by preparative TLC with petroleum:EtOAc (2:1)

出典と根拠

ORDレコード
ord-672b6f16f4414f8c9913d70350e21785
出典データセット
uspto-grants-2010_07
特許番号
US07754745B2

反応ノート

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