Acetic Acid → HCID 66921947, compound

HRID 1361470Notes

Reaction equation

HRID 1361470 reaction equation
II.C(O)(=O)C.P(=O)(O)(O)O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=O)=[C:15]([Cl:28])[CH:14]=1>C(OCC)(=O)C.O>[Cl:28][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[CH2:19][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[NH2:12]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 807IodineHCID 1004Phosphoric AcidHCID 30165104-Amino-2,4'-dichlorobenzophenone

Product 1

HCID 66921947HCID 66921947, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodine (1 g) and 50 mL of acetic acid were mixed together, 2.53 g of 50% phosphoric acid was added thereto, and the mixture was heated with stirring to reflux. Subsequently, a mixture composed of 3.2 g of (4-amino-2-chlorophenyl)-(4′-chlorophenyl)methanone and 15 mL of acetic acid were added dropwise to the mixed solution. This solution was heated under reflux for 134 hr, was then cooled and was poured into water. Ethyl acetate was added to the mixed solution followed by separation and washing with brine. The ethyl acetate layer was concentrated to give 3.0 g of 3-chloro-4-(4-chlorobenzyl)aniline (yield 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. additionwere added dropwise to the mixed solution
  4. temperatureThis solution was heated
  5. temperatureunder reflux for 134 hr
  6. temperaturewas then cooled
  7. customfollowed by separation
  8. washwashing with brine
  9. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-7ce953cc1aa84ee8b28dbd47419eca39
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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