Acetyl chloride → HCID 14537339, compound

HRID 653457Notes

Reaction equation

HRID 653457 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[C:6]2[S:12][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:14][C:5]1=2)[CH3:2].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([N:3]([CH:4]1[CH2:9][CH2:8][S:7](=[O:10])(=[O:11])[C:6]2[S:12][C:13]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:14][C:5]1=2)[C:26](=[O:28])[CH3:27])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9879717HCID 9879717, compound

Product 1

HCID 14537339HCID 14537339, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-(N-ethylamino)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (1.2 g, 0.0035 mol) in THF (30 ml) and triethylamine (1.1 ml, 0.79 g, 0.0078 mol) under N2 was added dropwise at room temperature a solution of acetyl chloride (0.26 ml, 0.28 g, 0.0036 mol) in THF (15 ml). After 2 hours, the mixture was poured into a saturated solution of NaHCO3 and extracted with ethyl acetate (3x). The organic extracts were dried, filtered and concentrated to dryness to yield 1.0 g (83%) of product.

Workup

  1. extractionextracted with ethyl acetate (3x)
  2. customThe organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-657f3fceb16840f78798750495a5af47
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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