Acetic Acid → HCID 21440368, compound

HRID 602503Notes

Reaction equation

HRID 602503 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[Cl:15])[CH3:2].C(O)(=O)C>O1CCCC1>[CH2:1]([O:3][C:4](=[O:16])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[Cl:15])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 3400859HCID 3400859, compound

Product 1

HCID 21440368HCID 21440368, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (ice/water bath) vigorously stirred solution of crude (2-Chloro-4-nitrophenyl)-carbamic acid ethyl ester (5.8 g, 21.8 mmol) in tetrahydrofuran (THF) (100 mL) and acetic acid (12 mL) zinc powder (20 g) was added by small portions maintaining the temperature below 40° C. The mixture was allowed to warm slowly to room temperature and after reaction completion (1 hour) it was filtered via a plug of SiO2 (20 g) with ethyl acetate as an eluent. The obtained solution was evaporated in vacuo and the crude yellow solid residue (4.9 g) was purified by precipitation from tetrahydrofuran (THF)/heptane to give 3.00 g of the title compound as pale yellow solid, yield 56%. LC/MS (m/z) 214, 216 (M+); RT=1.18, (UV, ELSD) 86%, 97%. 1H NMR (DMSO-d6): 1.18 (br. t, 3H), 4.02 (q, 2H), 5.29 (s, 2H, NH2), 6.45 (dd, 1H), 6.61 (d, 1H), 6.98 (br. d, 1H), 8.52 (br. s, NHCO).

Workup

  1. temperaturemaintaining the temperature below 40° C
  2. customafter reaction completion (1 hour) it
  3. filtrationwas filtered via a plug of SiO2 (20 g) with ethyl acetate as an eluent
  4. customThe obtained solution was evaporated in vacuo
  5. customthe crude yellow solid residue (4.9 g) was purified by precipitation from tetrahydrofuran (THF)/heptane

Sources & evidence

ORD record
ord-dbbb1d87d28b40ec9ffffb3b7f506583
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

Loading…