Ethyl Acetate → HCID 43518346, compound

HRID 1184373Notes

Reaction equation

HRID 1184373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=1[N+:18]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].CCOC(C)=O>C1COCC1.O>[NH2:18][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:10]=1[S:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:14]#[N:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 595489374-(2,5-Dichlorophenylthio)-3-nitrobenzonitrile

Product 1

HCID 43518346HCID 43518346, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A solution of compound 27 (11.8 g, 36.36 mmol) in THF (200 mL) was combined with a solution of sodium hydrosulfite (37.98 g, 218.16 mmol) in water (50 mL). The combined solution was stirred vigorously overnight at 45° C. The reaction was monitored by TLC (25% EtOAc in hexanes), and was complete after 16 hrs as indicated by absence of the starting material. The reaction was removed from heat and THF was evaporated. Aqueous solution was filtered to yield a white solid. The solid was washed with water and dried in a vacuum oven overnight to yield compound 28 (9.077 g, 97% HPLC purity, 84.6% yield). 1H NMR (500 MHz, DMSO-d6): δ 7.55 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.28 (dd, J1=2 Hz, J2=7 Hz, 1H), 7.19 (d, J=2 Hz, 1H), 6.99 (dd, J1=2 Hz, J2=8 Hz, 1H), 6.50 (d, J=2 Hz, 1H), 6.04 (s, 2H).

Workup

  1. waitwas complete after 16 hrs
  2. customThe reaction was removed
  3. temperaturefrom heat
  4. customTHF was evaporated
  5. filtrationAqueous solution was filtered
  6. customto yield a white solid
  7. washThe solid was washed with water
  8. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-bc2c3d25e2454a859a066126d0e80e60
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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