Hydrochloric Acid → HCID 67047896, compound

HRID 1907112Notes

Reaction equation

HRID 1907112 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]([C:13]#[N:14])=[C:8]([S:11][CH3:12])SC)([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[C:25]([F:26])=[CH:24][C:20]([C:21]([NH2:23])=O)=[C:19]([F:27])[CH:18]=1.[H-].[Na+].Cl.CN(C=[O:35])C>O>[C:1]([O:5][C:6]([C:7]1[C:13](=[O:35])[NH:14][C:21]([C:20]2[CH:24]=[C:25]([F:26])[C:17]([Cl:16])=[CH:18][C:19]=2[F:27])=[N:23][C:8]=1[S:11][CH3:12])=[O:15])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 219303404-chloro-2,5-difluorobenzamideHCID 53253389HCID 53253389, compound

Product 1

HCID 67047896HCID 67047896, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Cyano-3,3-bis-methylsulfanyl-acrylic acid tert-butyl ester (2.94 g, 12 mmol) and 4-chloro-2,5-difluorobenzamide (2.29 g, 12 mmol) were combined in 50 mL DMF and 60% sodium hydride (1.0 g, 25 mmol) was added in a single portion. After 1 hour, the reaction mixture was added to water and the neutralized with 2N HCl. The product was extracted with ether, dried, filtered and concentrated. The product was triturated with 30% diethyl ether/hexane to give 1.85 g of a white solid that was then heated in methanol overnight. The solid that formed when the reaction mixture cooled was filtered, rinsed with a small amount of cold methanol, and dried to give the title compound as a yellow solid (1.45 g, 31% yield for the two steps): 1H NMR (DMSO-d6): δ 13 (br s, 1H), 7.8-8.0 (m, 2H), 2.4 (s, 3H), 1.5 (s, 9H).

Workup

  1. extractionThe product was extracted with ether
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was triturated with 30% diethyl ether/hexane

Sources & evidence

ORD record
ord-0c6dd1466d5a4b499900700f24459973
Source dataset
uspto-grants-2013_12
Patent number
US08598085B2

Reaction notes

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