Triethylamine → N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide

HRID 1111402ノート

反応式

HRID 1111402 の反応式
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.ClC(OCCCC)=O.Cl.[O:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]([NH2:35])[C:33]#[N:34]>O1CCCC1>[C:33]([CH:32]([NH:35][C:8]([C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH3:7])=[O:10])[C:28]1[O:27][CH:31]=[CH:30][CH:29]=1)#[N:34]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 13075762HCID 13075762、化合物

生成物 1

HCID 14579913N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide収率 63.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4.71 g of 2,4-dimethylthiazole-5-carboxylic acid was suspended in 70 ml of tetrahydrofuran, and 6.67 g of triethylamine was added. The mixture was stirred. While it was cooled to -10° to -5° C., 4.10 g of n-butyl chloroformate was added, and the mixture was stirred at this temperature for 30 minutes, and then 4.03 g of alpha-(2-furyl)-alpha-aminoacetonitrile hydrochloride was added. The mixture was stirred at room temperature for 5 hours, and then left to stand overnight. The precipitate was separated by filtration and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Elution with hexane/ethyl acetate gave 4.20 g (yield 53.6%) of the desired N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide.

後処理

  1. temperatureWhile it was cooled to -10° to -5° C.
  2. stirringthe mixture was stirred at this temperature for 30 minutes
  3. stirringThe mixture was stirred at room temperature for 5 hours
  4. waitleft
  5. customThe precipitate was separated by filtration
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography
  9. washElution with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-1a2c2fc7423347f5b2da08d284023eb1
出典データセット
uspto-grants-1990_12
特許番号
US04980363

反応ノート

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