Benzidine sulfate → 3,7-Diaminodibenzothiophene-5,5-dioxide

HRID 376734

Reaction equation

HRID 376734 reaction equation
[S:1]([OH:5])(O)(=O)=[O:2].[C:6]1([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1>S(=O)(=O)(O)O>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]2[C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=3[S:1](=[O:5])(=[O:2])[C:12]=2[CH:11]=1

Participants

3

Reactant 1

HCID 88797Benzidine sulfate

Product 1

HCID 804123,7-Diaminodibenzothiophene-5,5-dioxideYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

The title compound was prepared as described in U.S. Pat. Nos. 2,590,632 and 2,620,343. At 10° C., 30 g of benzidine sulfate was added, in portions, to 100 ml of fuming sulfuric acid. After the addition, the reaction was maintained at 70° C. for 18 hours, cooled and poured into 250 g of cracked ice. The beige solid was collected, washed with water and saturated sodium bicarbonate yielding a yellow solid. The yellow solid was stirred with bicarbonate solution 2×, collected, washed with large volumes of water, and dried in vacuo to give 22.66 g (87%) of the desired product.

Workup

  1. customThe title compound was prepared
  2. additionAfter the addition
  3. temperaturecooled
  4. customThe beige solid was collected
  5. washwashed with water and saturated sodium bicarbonate yielding a yellow solid
  6. customcollected
  7. washwashed with large volumes of water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5d43279c26b04d69a33773e9367040ec
Source dataset
uspto-grants-2000_02
Patent number
US06022307

Linked notes

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