Phosgene → 2,4-Dimethoxy-1,3-thiazole-5-carbaldehyde

HRID 583789ノート

反応式

HRID 583789 の反応式
[CH3:1][O:2][C:3]1[S:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.C1(N(C)[CH:17]=[O:18])C=CC=CC=1.P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)=O.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[S:4][C:5]([CH:17]=[O:18])=[C:6]([O:8][CH3:9])[N:7]=1

参加物

7

反応物 5

HCID 6371PhosgeneHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 67749Trifluoromethanesulfonic anhydrideHCID 22342547HCID 22342547、化合物

生成物 1

HCID 223425452,4-Dimethoxy-1,3-thiazole-5-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 2,4-dimethoxythiazole (0.01 mol), which may be prepared as described in Step (a) above, in dichloromethane is added N-phenyl-N-methylformamide (0.01 mol) and phosphorous oxychloride (POCl3, 0.01 mol), or optionally phosgene or trifluoromethanesulfonic acid anhydride instead of POCl3, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the mixture is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 2,4-dimethoxythiazole-5-carboxaldehyde, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

後処理

  1. customReaction progress

出典と根拠

ORDレコード
ord-7d864eb5c8f44f6aaf3dec010a192b4f
出典データセット
uspto-grants-2005_08
特許番号
US06924276B2

反応ノート

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