Hydrochloric Acid → 5-(tert-Butylamino)-6-chloropyrazine-2,3-dicarbonitrile

HRID 973027Notes

Reaction equation

HRID 973027 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[C:12](Cl)=[N:11][C:10]([C:14]#[N:15])=[C:9]([C:16]#[N:17])[N:8]=1.O.Cl>O1CCCC1>[C:1]([NH:5][C:12]1[C:7]([Cl:6])=[N:8][C:9]([C:16]#[N:17])=[C:10]([C:14]#[N:15])[N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6385Tert-ButylamineHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 145764275-(tert-Butylamino)-6-chloropyrazine-2,3-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-Butylamine, 7.3 g (.1 mole), in 50 ml of dry tetrahydrofuran was added dropwise under nitrogen to a solution of 10 g (0.05 mole) of 2,3-dichloro-5,6-dicyanopyrazine in 100 ml of tetrahydrofuran. The rate of addition was controlled so that the reactants did not exotherm to greater than 35° C. When the addition was complete, the reactants were stirred an additional half hour and then poured into 1 l. of water. After adjusting the pH to 1-2 with 10% HCl, the precipitated product was filtered and washed thoroughly with water. Crude product after drying was twice recrystallized from 1-chlorobutane to give light yellow crystals having a mp of 169°-173° C.

Workup

  1. additionThe rate of addition
  2. customdid not exotherm to greater than 35° C
  3. additionWhen the addition
  4. additionpoured into 1 l
  5. filtrationthe precipitated product was filtered
  6. washwashed thoroughly with water
  7. customCrude product after drying
  8. customwas twice recrystallized from 1-chlorobutane
  9. customto give light yellow crystals

Sources & evidence

ORD record
ord-ac0d9be441a54811854b8d842fd3ce51
Source dataset
uspto-grants-1977_10
Patent number
US04054655

Reaction notes

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