Acetone → Cyprazine

HRID 370608

Reaction equation

HRID 370608 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C([N:7]([CH2:10]C)[CH2:8][CH3:9])C.C1(C2[N:20]=[C:19]([Cl:21])[N:18]=[C:17](Cl)[N:16]=2)CC1.[CH3:23]C(C)=O>>[Cl:21][C:19]1[N:18]=[C:17]([NH:4][CH:1]2[CH2:3][CH2:2]2)[N:16]=[C:10]([NH:7][CH:8]([CH3:23])[CH3:9])[N:20]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6363Isopropylamine2×HCID 8471TriethylamineHCID 189652202,4-Dichloro-6-cyclopropyl-1,3,5-triazine

Product 1

HCID 24738Cyprazine

Procedure

A mixture of 9.5 g of isopropylamine and 16.2 g of triethylamine was added drop-by-drop to a stirred solution of 33 g of 9A in 500 ml of dry acetone at room temperature. The reaction was monitored by thin layer chromatography and further isopropylamine was added until only one product was shown. The solvent was evaporated, and the residue was treated with a 1:1 v:v mixture of ice water and ether. The ether phase was separated and dried (MgSO4), and the solvent was evaporated to give 2-chloro-4-(cyclopropylamino)-6-(1-methylethylamino)-1,3,5-triazine (9B), as a white solid, m.p.: 160.5°-161° C.

Workup

  1. additionwas added until only one product
  2. customThe solvent was evaporated
  3. additionthe residue was treated with a 1:1 v
  4. additionv mixture of ice water and ether
  5. customThe ether phase was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2d7bbb286e8c41f193233fc80a915127
Source dataset
uspto-grants-1985_07
Patent number
US04528027

Linked notes

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