Triethylamine → HCID 19045468, compound

HRID 1781408Notes

Reaction equation

HRID 1781408 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:11]([OH:14])(=O)=[O:12])[CH:7]=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].C(N(CC)CC)C.CN(C)C(=O)C.O=P(Cl)(Cl)[Cl:30]>C1S(=O)(=O)CCC1.C(#N)C>[C:1]([C:4]1[CH:5]=[C:6]([S:11]([Cl:30])(=[O:14])=[O:12])[CH:7]=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 184047473-Acetyl-4-hydroxybenzene-1-sulfonic acid

Product 1

HCID 19045468HCID 19045468, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 3-acetyl-4-hydroxy-benzenesulfonic acid (3.0 g) (prepared according to T. Pfliegel et. al., Acta Chim. Acad. Sci. Hung., 98(2) 231-240(1978)) in tetramethylenesulfone (6 mL) and acetonitrile (6 mL) under argon was treated with triethylamine (1.94 mL) and N,N-dimethylacetamide (0.32 mL). This was stirred for 30 min and POCl3 was added dropwise maintaining the temperature below. 25° C. The reaction was stirred for 24 hr, cooled to 10° C. and quenched with water (15 mL). This mixture was warmed to 60° C. and stirred for 1 hr, at which point a precipitate formed which was then filtered and dried to give 2.34 g (72%) of 3-acetyl-4-hydroxybenzenesulfonylchloride.

Workup

  1. temperaturemaintaining the temperature below
  2. custom25° C
  3. stirringThe reaction was stirred for 24 hr
  4. customquenched with water (15 mL)
  5. temperatureThis mixture was warmed to 60° C.
  6. stirringstirred for 1 hr, at which point a precipitate
  7. customformed which
  8. filtrationwas then filtered
  9. customdried

Sources & evidence

ORD record
ord-a21fa8981c44402c978c9e3b60a57916
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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