Phosphorus oxychloride → 1-Chlorosulfonylanthraquinone

HRID 1983204

Reaction equation

HRID 1983204 reaction equation
[C:1]1([S:17]([O-:20])(=O)=[O:18])[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Na+].O=P(Cl)(Cl)[Cl:24].S1(CCCC1)(=O)=O>C(#N)C>[Cl:24][S:17]([C:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1)(=[O:20])=[O:18]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 517266Sodium anthraquinone-1-sulfonate

Product 1

HCID 3443001-Chlorosulfonylanthraquinone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

Sodium anthraquinone-1-sulfonate (50.0 g) was combined with POCl3 (31 mL) and a 1:2 (v/v) mixture of sulfolane (100 mL) and acetonitrile (200 mL). The mixture was stirred and heated to 110° C. under a nitrogen atmosphere for 44 hours. The mixture was allowed to cool to room temperature and was then further cooled in a refrigerator. The mixture was filtered and the filtrate was poured onto ice in a beaker and this mixture was stirred for 1 hour. The brown precipitate was filtered, washed with deionized water, dried in air and then further dried overnight in a vacuum oven at 45° C. and less than lmmHg pressure to give 12.08 g of the product as a brown solid.

Workup

  1. temperatureto cool to room temperature
  2. temperaturewas then further cooled in a refrigerator
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was poured onto ice in a beaker
  5. stirringthis mixture was stirred for 1 hour
  6. filtrationThe brown precipitate was filtered
  7. washwashed with deionized water
  8. customdried in air
  9. customfurther dried overnight in a vacuum oven at 45° C. and less than lmmHg pressure

Sources & evidence

ORD record
ord-5a002447e21246498b46f682a24b10f9
Source dataset
uspto-grants-2009_06
Patent number
US07541389B2

Linked notes

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