Triethylamine → HCID 69892953, compound

HRID 48342Notes

Reaction equation

HRID 48342 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]([CH3:30])[C:20]([CH2:22][NH:23]C(=O)C(C)(C)C)=[O:21])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C>C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH:9]=[CH:10][C:11]1=[N:23][CH2:22][C:20](=[O:21])[N:19]([CH3:30])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]1=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22742421(E)-N-[[N-[2-[3-(3,4-dichlorophenyl)acryloyl]phenyl]-N-methylcarbamoyl]methyl]pivalamide

Product 1

HCID 69892953HCID 69892953, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

65 mg (0.14 mmol) of (E)-N-[[N-[2-[3-(3,4-dichlorophenyl)acryloyl]phenyl]-N-methylcarbamoyl]methyl]pivalamide were dissolved in 5 ml of ethyl acetate saturated with hydrogen chloride and were stirred at room temperature for 30 minutes. The solvent was removed by evaporation and the residue dissolved in 5 ml of methanol and 40 mg (0.04 mmol) of triethylamine added. After 2 hours at room temperature the solvent was removed by evaporation and the residue chromatographed on silica gel using ethyl acetate/petrol 2:1 for the elution. There was obtained 33 mg of (E)-5-(3,4-dichlorostyryl)-1,3-dihydro-1-methyl-2H-benzo-1,4-diazepin-2-one as a pale yellow foam. MS: m/e 344.9 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue dissolved in 5 ml of methanol
  3. customAfter 2 hours at room temperature the solvent was removed by evaporation
  4. customthe residue chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-a1987d87efc2427fb6f8b133fffdbeae
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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