Water → HCID 57500678、化合物

HRID 604376ノート

反応式

HRID 604376 の反応式
O=[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[NH:3]1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:30].O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:30][C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[N:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 57500672HCID 57500672、化合物

生成物 1

HCID 57500678HCID 57500678、化合物収率 47%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

Methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate (1.0 eq, 0.62 g, 2.38 mmol) was suspended in toluene. DIEA (1.5 eq, 122 ul, 3.57 mmol) and POCl3 (2.3 eq, 507 ul, 5.47 mmol) were added and the mixture vigorously stirred at 120° C. for 1 hour. Water, ice and CH2Cl2 were added and the resulting emulsion filtered through celite. The organic phase was decanted and the aqueous phase further extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and the solvent removed in vacuo to afford methyl 4-chlorothiazolo[4,5-c]quinoline-7-carboxylate (0.31 g, 47% yield). LCMS (ES): >90% pure, m/z 279[M+1]+.

後処理

  1. filtrationthe resulting emulsion filtered through celite
  2. customThe organic phase was decanted
  3. extractionthe aqueous phase further extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-78b193431a0d486aa97a2ee1e2909174
出典データセット
uspto-grants-2011_03
特許番号
US07910600B2

反応ノート

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