Hydrochloric Acid → 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide

HRID 1393847Notes

Reaction equation

HRID 1393847 reaction equation
CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:30]([N:37]([S:42]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH2:38][C:39](O)=[O:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH2:53][C:54]1[S:55][S:56][C:57](=[S:59])[N:58]=1.Cl>CN(C)C=O>[CH2:30]([N:37]([S:42]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH2:38][C:39]([NH:53][C:54]1[S:55][S:56][C:57](=[S:59])[N:58]=1)=[O:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7188402-{Benzyl[(4-methoxyphenyl)sulfonyl]amino}acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735329Xanthane hydride

Product 1

HCID 596805152-{benzyl[(4-methoxyphenyl)sulfonyl]amino}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-methylmorpholine (0.79 ml, 7.15 mmol), N-hydroxybenzotriazole (1.10 g, 7.15 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (1.37 g, 7.15 mmol) are added to a solution of 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}acetic acid (2.00 g, 5.96 mmol) in N,N-dimethylformamide (20 ml) while being cooled with ice, and stirred for 1 hour. Then, the mixture, with 3-amino-1,2,4-dithiazole-5-thione (1.08 g, 7.15 mmol) added thereto, was stirred for 5 hours at room temperature. The reaction, with 1N hydrochloric acid added thereto, was extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate water and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (3% methanol/chloroform), to give aimed 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 1) (0.883 g, 32%).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 5 hours at room temperature
  3. customThe reaction
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with sodium bicarbonate water and saturated brine successively
  6. dry with materialdried over sodium sulfate anhydride
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-6e0d4debfa3341219eac0ec958e44eed
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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