Diethyl Ether → HCID 58016053、化合物

HRID 2069100ノート

反応式

HRID 2069100 の反応式
S(Cl)(Cl)=O.[C:5]1([C:11]2[N:12]=[CH:13][S:14][C:15]=2C(O)=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N-:19]=[N+]=[N-].[Na+].C([O:25][CH2:26]C)C>C1C=CC=CC=1.O>[N:12]1[C:11]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:26](=[O:25])[NH:19][C:15]=2[S:14][CH:13]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 134413294-Phenylthiazole-5-carboxylic acid

生成物 1

HCID 58016053HCID 58016053、化合物収率 20%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Thionyl chloride (1 ml) was added to a suspension of 4-phenyl-1,3-thiazole-5-carboxylic acid (300 mg, 1.46 mmol) in 10 ml of dry benzene and the mixture was refluxed for 2 hours. The solvent and the excess of thionyl chloride were removed under reduced pressure; the residue was taken up using 10 ml of dry THF and cooled to 0° C. Sodium azide (1.5 mmol) dissolved in the minimal amount of water was quickly added and the resulting solution was stirred for 1 hour at room temperature. After pouring into 100 ml of cracked ice/H2O and extraction with diethyl ether (4×100 ml), the collected organic layers were dried over Na2SO4. The filtrate was gently evaporated under reduced pressure, the residue was dissolved in 10 ml of o-dichlorobenzene, and the resulting mixture was refluxed for 5-10 hours. The mixture was then cooled, and directly submitted to flash chromatography, elution with dichloromethane/methanol (99/1) afforded to the title compound.

後処理

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe solvent and the excess of thionyl chloride were removed under reduced pressure
  3. additionwas quickly added
  4. dry with materialthe collected organic layers were dried over Na2SO4
  5. customThe filtrate was gently evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in 10 ml of o-dichlorobenzene
  7. temperaturethe resulting mixture was refluxed for 5-10 hours
  8. temperatureThe mixture was then cooled
  9. washdirectly submitted to flash chromatography, elution with dichloromethane/methanol (99/1)

出典と根拠

ORDレコード
ord-d73b3b627b7c46f0a21e4a8156e9fe57
出典データセット
uspto-grants-2012_10
特許番号
US08299090B2

反応ノート

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