HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetate

HRID 336339
Notes
Print preview

Reaction equation

HRID 336339 reaction equation
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O>[C:1]1([C:7](=[N:14][CH:15]([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 6428002-Bromopyrazine

Product 1

HCID 10246971Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 67553
Tetrabutylammonium Iodide
Catalyst
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 2-((diphenylmethylene)amino)acetate (6.0 g, 22.47 mmol), 2-bromopyrazine (7.1 g, 44.90 mmol), potassium carbonate (9.30 g, 67.40 mmol) and tetrabutyl ammonium iodide (8.10 g, 22.40 mmol) in N-methyl-2-pyrrolidone (25 mL) was heated in a sealed tube at 110° C. for 16 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were washed with brine (25 mL) and dried over sodium sulfate. Removal of solvent under vacuum afforded crude product which was purified in Combi-Flash instrument using a gradient of methanol in chloroform. Yield: 4.90 g (63%). 1H NMR (300 MHz, DMSO-d6) δ: 1.16 (t, 3H), 4.07 (q, 2H), 5.26 (s, 1H), 7.18 (dd, 2H), 7.38-7.61 (m, 8H), 8.56 (d, 1H), 8.57 (d, 1H), 8.60 (s, 1H). MS (ES) MH+: 346.3 for C21H19N3O2.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe organic layers were washed with brine (25 mL)
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvent under vacuum
  5. customafforded crude product which
  6. customwas purified in Combi-Flash instrument

Sources & evidence

ORD record
ord-3c5640f5596048ceb5e6ad6d3633d084
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889671B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes