Hydrochloric Acid → HCID 14130307, compound

HRID 1708977Notes

Reaction equation

HRID 1708977 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[C:11]([O:17][CH2:18][C:19]#[CH:20])[C:12]=1[O:13][CH2:14][C:15]#[CH:16])N.[ClH:21]>C(O)(=O)C.[Cu](Cl)Cl>[Cl:21][C:8]1[CH:10]=[C:11]([O:17][CH2:18][C:19]#[CH:20])[C:12]([O:13][CH2:14][C:15]#[CH:16])=[C:6]([Cl:5])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 136563003-Chloro-4,5-bis[(prop-2-yn-1-yl)oxy]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 14130307HCID 14130307, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Sodium nitrite (1.33 g) was added to a solution of 3-chloro-4,5-dipropargyloxyaniline (4.47 g) in acetic acid (30 ml) and 35% hydrochloric acid (4 ml) at 0° C., followed by stirring at the same temperature for 1 hour. The resultant solution was poured into 35% hydrochloric acid (20 ml) containing copper chloride (2.35 g) at room temperature, and stirring was continued at 60° C. for 30 minutes. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with aqueous sodium carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography using toluene as an eluent to give 1,3-dichloro-4,5-dipropargyloxybenzene (3.60 g) as white crystals. m.p. 61°-63° C.

Workup

  1. stirringstirring
  2. waitwas continued at 60° C. for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium carbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cb227abb8ba4a65aef7deaa2ec7f528
Source dataset
uspto-grants-1990_08
Patent number
US04946865

Reaction notes

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