Ammonia → HCID 57833611, compound

HRID 730089Notes

Reaction equation

HRID 730089 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=O)[C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([N:21](CC)CC)C.N.O1CCOCC1>S(Cl)(Cl)(=O)=O.CO>[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH2:21])=[O:18])[C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 4292989-Oxo-9H-thioxanthene-4-carboxylic acid

Product 1

HCID 57833611HCID 57833611, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24648Sulfuryl chlorideSolvent

Procedure

A sample of 9-oxo-9H-thioxanthene-4-carboxylic acid 1r (15 g, 58.7 mmol) was heated in sulfonyl chloride (70 mL) for 2 h. Excess sulfonyl chloride was removed via evaporation. The residue was dissolved in tetrahydrofuran (200 mL), and triethylamine (16.4 mL, 117.4 mmol) and a 0.5 M solution of ammonia in dioxane (176 mL, 88.5 mmol) were added. Methanol (20 mL) was added, and the mixture was evaporated. Water and chloroform were added, and a precipitate formed. The precipitate was isolated via filtration, and yielded 3.5 g (25%) of title compound 2r. The organic layer was separated, dried, filtered, and evaporated to yield 11 g of recovered 1r.

Workup

  1. customExcess sulfonyl chloride was removed via evaporation
  2. dissolutionThe residue was dissolved in tetrahydrofuran (200 mL)
  3. customthe mixture was evaporated
  4. additionWater and chloroform were added
  5. customa precipitate formed
  6. customThe precipitate was isolated via filtration

Sources & evidence

ORD record
ord-249d639a79334917814542dc00dd69cd
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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