Triethylamine → HCID 14537341, compound

HRID 653466Notes

Reaction equation

HRID 653466 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[C:5]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:4]1=2.C(N(CC)CC)C.[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27].C([O-])(O)=O.[Na+]>C1COCC1>[C:25]([NH:2][CH:3]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[C:5]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:4]1=2)(=[O:29])[CH:26]([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 516892Sodium BicarbonateHCID 13911595HCID 13911595, compound

Product 1

HCID 14537341HCID 14537341, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under N2 was added 5,6-dihydro-4-amino-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxidehydrochloride (3.2 g, 0.01 mol), triethylamine (2.2 g, 0.022 mol) and THF (100 ml). The mixture was stirred at room temperature while a solution of isobutyryl chloride (1.12 g, 0.0105 mol) in THF (10 ml) was added dropwise. After 18 hours, the mixture was poured onto saturated NaHCO3 and the suspension was extracted with ethyl acetate (3X). The combined organic extracts were dried, filtered and concentrated to dryness to yield 3.2 g (91%) of product.

Workup

  1. additionwas added dropwise
  2. extractionthe suspension was extracted with ethyl acetate (3X)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32cd9157039549949c88cf468e3b8b28
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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