Dimethylformamide → n-{2-[4-(1,1-Dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}benzamide

HRID 724598Notes

Reaction equation

HRID 724598 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH:18]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CN(C=O)C>C(Cl)Cl>[O:22]=[S:21]1(=[O:23])[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:12][CH:13]=2)=[CH:18][C:19](=[O:24])[NH:20]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 21878746HCID 21878746, compound

Product 1

HCID 58746686n-{2-[4-(1,1-Dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}benzamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23-F (7.0 mg, 0.019 mmol) and triethylamine (8 μL, 0.0573 mmol) were dissolved in methylene chloride (0.25 mL). Benzoyl chloride (2.8 μL, 0.0239 mmol) was added and the reaction was allowed to stir at room temperature. DMF (0.25 mL) was added and allowed to stir overnight. The reaction was chromatographed on a 21 mm Luna C18 column using a 10–90% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 12.5 mL per minute over a 30 minute period. The major fraction was lyophilized to give a white powder (2.0 mg, 29%). 1H NMR (500 MHz, CD3OD): δ 7.91 (d, J=8.7 hz, 2H), 7.81 (d, J=8.9 Hz, 2H), 7.52 (d, J=8.8 Hz, 2H), 7.43 (m, 3H), 6.97 (s, 1H), 6.69 (br s, 1H), 3.47 (t, J=7.0 Hz, 2H), 2.91 (t, J=7.0 Hz, 2H); LCMS found for C18H17N2O4S (M+H)+: m/z=357.

Workup

  1. stirringto stir overnight
  2. customThe reaction was chromatographed on a 21 mm Luna C18 column
  3. customover a 30 minute

Sources & evidence

ORD record
ord-6d59331e96c34eb887117fa321e032ea
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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