Acetic Acid → HCID 14028596, compound

HRID 2119237Notes

Reaction equation

HRID 2119237 reaction equation
[I:1][C:2]1[CH:7]=C(N)C=[CH:4][C:3]=1[C:9]1[CH:15]=[CH:14][C:12](N)=[CH:11][C:10]=1[I:16].F[B-](F)(F)F.[H+].N([O-])=[O:24].[Na+].[C:27]([OH:30])(=O)[CH3:28]>>[OH:24][C:12]1[CH:14]=[CH:15][C:9]([C:3]2[CH:4]=[CH:28][C:27]([OH:30])=[CH:7][C:2]=2[I:1])=[C:10]([I:16])[CH:11]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 28118Tetrafluoroboric acidHCID 2981912,2'-diiodo-4,4'-diaminobiphenylHCID 23668193Sodium Nitrite

Product 1

HCID 14028596HCID 14028596, compound

Conditions

Temperature
-5 °C

Procedure

Glacial acetic acid (200 ml) and 2,2'-diiodobenzidine (20.0 g, 49 mmol) were stirred at room temperature for 20 minutes, and then 100 ml 48% tetrafluoroboric acid was added to the solution. After 30 minutes, the acidic solution was cooled to -5° C., and a sodium nitrite solution (7.2 g NaNO2 in 80 ml water) was slowly added to maintain the temperature below 0° C. The reaction was stirred for 1 hour at 0° C., and the precipitate which formed was filtered and dried for 18 hours under vacuum. The dried product was added over a period of 1 hour to a solution of 2 L water containing 30 ml 85% phosphoric acid at 75° C.

Workup

  1. temperatureto maintain the temperature below 0° C
  2. customthe precipitate which formed
  3. filtrationwas filtered
  4. customdried for 18 hours under vacuum
  5. additionThe dried product was added over a period of 1 hour to a solution of 2 L water containing 30 ml 85% phosphoric acid at 75° C.

Sources & evidence

ORD record
ord-15213baf8dc74b69925a08439f223be2
Source dataset
uspto-grants-1987_07
Patent number
US04683340

Reaction notes

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