Sodium hydride → HCID 68819703, compound

HRID 1819743Notes

Reaction equation

HRID 1819743 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[N:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[H-].[Na+].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)=[O:26]>CN(C=O)C>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([S:11]([N:10]=[C:2]2[N:3]([CH2:24][C:25](=[O:26])[C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1]2)(=[O:12])=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 692722-Bromo-4'-methylacetophenoneHCID 178427428HCID 178427428, compound

Product 1

HCID 68819703HCID 68819703, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20 (930 mg, 3.01 mmol) in DMF (15 mL) at room temperature was added NaH. After the effervescence subsided, 2-bromo-4′-methylacetophenone (775 mg, 3.36 mmol) was added. The reaction was first stirred at room temperature for an hour and then heated at 80° C. until completion (by TLC). The mixture was allowed to cool before being poured on ice (400 mL). A precipitate dropped out. It was filtered and washed with cold water and dried to give a pale yellow powder in quantitative yield: mp 180-182° C.; 1H-NMR (DMSO-d6) 2.35 (s, 3H), 2.43 (s, 3H), 5.86 (s, 2H), 7.33 (m, 3H), 7.42 (m, 3H), 7.57 (d, 1H), 7.64 (d, 2H), 7.91 (d, 1H), 7.97 (d, 2H); Anal. (C23H20N2O3S2) C, H, N.

Workup

  1. temperatureheated at 80° C. until completion (by TLC)
  2. temperatureto cool
  3. additionbefore being poured on ice (400 mL)
  4. additionA precipitate dropped out
  5. filtrationIt was filtered
  6. washwashed with cold water
  7. customdried
  8. customto give a pale yellow powder in quantitative yield

Sources & evidence

ORD record
ord-e5486246c4774410ab1e746ff800f791
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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