Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]-2-fluoro-5-nitrobenzoate → HCID 21873648, compound

HRID 885674Notes

Reaction equation

HRID 885674 reaction equation
C([O:3][C:4]([C:6]1[C:7]([F:17])=[CH:8][C:9]2[S:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=1)=O)C.C(OC(=O)C1C=C([N+]([O-])=O)C(SCC(OCC)=O)=CC=1F)C>C(O)(=O)C.[Fe]>[F:17][C:7]1[C:6]([CH:4]=[O:3])=[CH:16][C:10]2[NH:11][C:12](=[O:15])[CH2:13][S:14][C:9]=2[CH:8]=1

Participants

5

Reactant 2

HCID 59560604Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]-2-fluoro-5-nitrobenzoateHCID 59560644HCID 59560644, compound

Product 1

HCID 21873648HCID 21873648, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

7-Fluoro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid ethyl ester. To a solution of 4-ethoxycarbonylmethylsulfanyl-2-fluoro-5-nitro-benzoic acid ethyl ester (2.7 g, 8.2 mmol) in acetic acid (50 mL) was added iron (4.8 g, 86 mmol) and the suspension was heated to 80° C. and stirred for 2 h. The reaction mixture was filtered and the filtrate was partitioned between H2O and EtOAc (1×200 mL; 2×100 mL). The combined organic layers were washed with brine (300 mL), dried (MgSO4), filtered and concentrated to provide 1.7 g (82%) of the title compound as a tan solid. MS (ESI): exact mass calculated for C11H10FNO3S, 255.04; m/z found, 256.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.75 (br s, 1H), 7.46 (d, J=6.1, 1H), 7.12 (d, J=10.4, 1H), 4.40 (q, J=7.1, 2H), 3.48 (s, 2H), 1.38 (t, J=7.1, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was partitioned between H2O and EtOAc (1×200 mL; 2×100 mL)
  3. washThe combined organic layers were washed with brine (300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01848703f26943799c5c022443007e77
Source dataset
uspto-grants-2012_08
Patent number
US08242275B2

Reaction notes

Loading…