Triethylamine → HCID 21873648、化合物

HRID 1518014ノート

反応式

HRID 1518014 の反応式
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([S:14][CH2:15][C:16](OCC)=[O:17])=[CH:7][C:6]=1[F:21])C.C(OC(=O)C1C=C([N+]([O-])=O)C(F)=CC=1F)C.CCN(CC)CC.SCC(OCC)=O>C(Cl)Cl>[F:21][C:6]1[C:5]([CH:4]=[O:3])=[CH:10][C:9]2[NH:11][C:16](=[O:17])[CH2:15][S:14][C:8]=2[CH:7]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoateHCID 59560604Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]-2-fluoro-5-nitrobenzoate

生成物 1

HCID 21873648HCID 21873648、化合物収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Ethoxycarbonylmethylsulfanyl-2-fluoro-5-nitro-benzoic acid ethyl ester. To a solution of 2,4-difluoro-5-nitro-benzoic acid ethyl ester (7.0 g, 0.030 mol) in CH2Cl2 (125 mL) was added Et3N (5.0 mL, 36 mmol) at 0° C. Following the addition of ethyl 2-mercaptoacetate (3.30 mL, 30.3 mmol), the solution was warmed to RT and stirred for 18 h. The reaction mixture was partitioned between H2O and CH2Cl2 (400 mL). The organic layer was washed with 0.05 M HCl (200 mL), brine (200 mL), dried (MgSO4), filtered and concentrated to provide 9.6 g (96%) of the title compound as a tan solid. MS (ESI): exact mass calculated for C13H14FNO6S, 331.05; m/z not found. 1H NMR (500 MHz, CDCl3): 8.88 (d, J=6.9, 1H), 7.14 (d, J=11.4, 1H), 4.41 (q, J=7.2, 2H), 4.29 (q, J=7.2, 2H), 3.75 (s, 2H), 1.40 (t, J=7.2, 3H), 1.29 (t, J=7.2, 3H).

後処理

  1. customThe reaction mixture was partitioned between H2O and CH2Cl2 (400 mL)
  2. washThe organic layer was washed with 0.05 M HCl (200 mL), brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-38674fad47e841ddaf83728a0fc75ce4
出典データセット
uspto-grants-2012_07
特許番号
US08232391B2

反応ノート

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