Hydrochloric Acid → 8-Oxatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene-5-sulfonyl chloride

HRID 1071576Notes

Reaction equation

HRID 1071576 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=1.[ClH:15].N([O-])=O.[Na+].[S:20](=[O:22])=[O:21]>C(O)(=O)C.[Cu](Cl)Cl.C1C=CC=CC=1.O>[CH:4]1[C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=[C:2]([S:20]([Cl:15])(=[O:22])=[O:21])[CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 200613-DibenzofuranamineHCID 23668193Sodium Nitrite

Product 1

HCID 221793058-Oxatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene-5-sulfonyl chloride

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

3-Aminodibenzofuran (10 g, 54.6 mol) was diazotized by dissolving in 180 mL glacial acetic acid, 50 mL water, and 14 mL concentrated hydrochloric acid at 0° C. and adding 15 mL of a 5.5 M aqueous solution of sodium nitrite. The resulting mixture was stirred for 1 hour before pouring into a solution of copper(II)chloride (2.0 g, 14.9 mmol) in 240 mL of a 1:1 mixture of benzene and glacial acetic acid saturated with sulfur dioxide. This mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction was partitioned between water and chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, filtered, and concentrated to give the title compound as a yellowish solid; melting point=142-144° C.

Workup

  1. stirringstirred for 16 hours
  2. customThe reaction was partitioned between water and chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85d5e1884c8d44ecb394c4dae678537b
Source dataset
uspto-grants-2005_06
Patent number
US06906092B2

Reaction notes

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