Dimethylamine → N-(3-(dimethylamino)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

HRID 1258384Notes

Reaction equation

HRID 1258384 reaction equation
Cl[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[N:13]/[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])/[CH:3]=1.[CH3:22][NH:23][CH3:24]>C1COCC1>[CH3:22][N:23]([CH3:24])[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:13][S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 22524852(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)thiophene-2-sulfonamide

Product 1

HCID 67329790N-(3-(dimethylamino)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

33.5 mg (E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide was dissolved in 2 ml THF, to which was added 0.4 ml dimethylamine in THF solution (2 M). The wine-red solution was stirred at r.t. for 10 min and concentrated. The residue was suspended in 50 ml ethyl acetate and washed with water and brine. Dried over Na2SO4, the organic phase was filtered and the filtrate was concentrated to dryness affording the title compound 36 mg (100%) as a wine-red solid, m.p.: 183-185° C.

Workup

  1. concentrationconcentrated
  2. washwashed with water and brine
  3. dry with materialDried over Na2SO4
  4. filtrationthe organic phase was filtered
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-122376370a2649bcb23012153ad666ad
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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