Water → HCID 67168460, compound

HRID 872837Notes

Reaction equation

HRID 872837 reaction equation
[Br:1][C:2]1[O:3][C:4]([CH:7]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][N+:9]([O-])=O)=[CH:5][CH:6]=1.O.[OH-].[Na+]>C(O)(=O)C.Cl.[Zn]>[Br:1][C:2]1[O:3][C:4]([CH:7]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][NH2:9])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67169620HCID 67169620, compound

Product 1

HCID 67168460HCID 67168460, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

Zinc powder (0.80 g, 0.01224 mol) was added to 2-bromo-5-(2-nitro-1-phenylsulfanylethyl)furan (0.60 g, 0.001828 mol) dissolved in the mixture of glacial acetic acid (24 ml) and concentrated hydrochloric acid (2.4 ml) at 80° C. in nitrogen atmosphere. The mixture was heated at 80° C. for 2.5 h. Then, 0.40 g (0.00612 mol) of zinc powder was added and the mixture was heated for 1 h. The reaction mixture was cooled and 36 ml of water was added. pH was adjusted to 9 by 2.5 M NaOH. The product was extracted into ethyl acetate. The organic phase was washed with water, dried and evaporated. 1H NMR (400 MHz, DMSO-d6): 2.87 (1H, distorted dd), 2.97 (1H, distorted dd), 4.41 (1H, t), 6.21 (1H, d), 6.45 (1H, d), 7.31 (5H, m).

Workup

  1. temperaturethe mixture was heated for 1 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted into ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f59e915b35014c7c9b031e000459b1ac
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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