Hydrochloric Acid → HCID 54915161, compound

HRID 493385Notes

Reaction equation

HRID 493385 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:21](Cl)(=[O:23])[CH3:22].Cl>C(=S)=S.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:11]1[CH:12]=[CH:13][C:14]([C:21](=[O:23])[CH3:22])=[CH:15][CH:16]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 69284Benzene, 1-nitro-3-phenoxy-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 54915161HCID 54915161, compound

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The compound 1-nitro-3-phenoxybenzene (10.17 g, 0.0473 mol) is put into solution in carbon disulphide (70 ml). Aluminium chloride (10.06 g, 0.076 mol) is added by portions at ambient temperature. The reaction medium is cooled down to 0° C. then acetyl chloride (2.4 ml, 0.038 mol) is added dropwise. The reaction medium is left to return to 23° C. then stirring is maintained for 5 hours, followed by cooling down again to 0° C., then the careful addition of ethyl acetate, crushed ice and 3 N hydrochloric acid. After decantation, the medium is extracted with ethyl acetate. The organic phase is washed with water, with a saturated solution of sodium carbonate then with a saturated solution of sodium chloride. It is then dried over sodium sulphate then evaporated. The residue obtained is adsorbed on silica then purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 1-4). After washing with diethyl ether, a yellow-coloured powder is obtained.

Workup

  1. waitThe reaction medium is left
  2. customto return to 23° C.
  3. temperatureis maintained for 5 hours
  4. temperatureby cooling down again to 0° C.
  5. extractionAfter decantation, the medium is extracted with ethyl acetate
  6. washThe organic phase is washed with water, with a saturated solution of sodium carbonate
  7. dry with materialIt is then dried over sodium sulphate
  8. customthen evaporated
  9. customThe residue obtained
  10. customthen purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 1-4)
  11. washAfter washing with diethyl ether
  12. customa yellow-coloured powder is obtained

Sources & evidence

ORD record
ord-e9b516c47f624b19b87cd08de2812c07
Source dataset
uspto-grants-2009_05
Patent number
US07534805B2

Reaction notes

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