Phosphorus oxychloride → HCID 22248864, compound

HRID 2179993Notes

Reaction equation

HRID 2179993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12]([CH2:20][CH3:21])=[N+:13]([O-])[CH:14]=[C:15]([CH2:17][CH3:18])[N:16]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:14]1[C:15]([CH2:17][CH3:18])=[N:16][C:11]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])=[C:12]([CH2:20][CH3:21])[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22490045HCID 22490045, compound

Product 1

HCID 22248864HCID 22248864, compound

Conditions

Temperature
60 °C

Procedure

The product from step 2 (3.3 g) is dissolved in POCl3 (25 mL) and the resulting solution stirred at 60° C. for 6 hours. The reaction mixture is cooled, and the volatiles are removed under reduced pressure. Flash chromatography (1-4% ethyl acetate in hexanes) affords 2-chloro-5-(2,4-dimethoxy-phenyl)-3,6-diethyl-pyrazine as a clear oil. MS: 307. H-1 NMR (400 MHz, CDCl3): 1.16 (t, 3H), 1.31 (t, 3H), 2.60 (q, 2H), 3.00 (q, 2H), 3.75 (s, 3H), 3.76 (s, 3H), 6.53 (d, 1H), 6.59 (dd, 1H), 7.19 (d, 1H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe volatiles are removed under reduced pressure

Sources & evidence

ORD record
ord-08d0f6d8478e4cdbb7df97330482d0d1
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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