Triethylamine → HCID 21873648, compound

HRID 1518014Notes

Reaction equation

HRID 1518014 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 21873648HCID 21873648, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-38674fad47e841ddaf83728a0fc75ce4
Source dataset
uspto-grants-2012_07
Patent number
US08232391B2

Reaction notes

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