Benzaldehyde → HCID 68119580, compound

HRID 1438838Notes

Reaction equation

HRID 1438838 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([CH:9]([CH2:11][CH3:12])[CH3:10])=[N:5][N:4]=[C:3]1[S:13][CH3:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH:15](=[N:1][N:2]1[C:7](=[O:8])[C:6]([CH:9]([CH2:11][CH3:12])[CH3:10])=[N:5][N:4]=[C:3]1[S:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 23050531HCID 23050531, compound

Product 1

HCID 68119580HCID 68119580, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

21.4 g of 4-amino-6-sec.-butyl-3-methylthio-1,2,4-triazin-5(4H)-one and 11.0 ml of benzaldehyde, dissolved in 50 ml of isopropanol, were briefly heated to the reflux temperature after adding 0.1 g of p-toluenesulfonic acid. On cooling to 0° C, 23.2 g of crude product crystallized out and were purified further by dissolving in 200 ml of boiling toluene. A small amount of a high-melting by-product crystallized out at 0° C and was filtered off and discarded. On concentration on a rotary evaporator, the mother liquor left 21.1 g (70%) of a pale oil which crystallized after trituration with a little methanol. The pure 4-benzylideneamino-6-sec.-butyl-3-methylthio-1,2,4-triazine-5 (4H)-one melted at 73° C.

Workup

  1. temperaturewere briefly heated to the reflux temperature
  2. custom23.2 g of crude product crystallized out
  3. customwere purified further
  4. dissolutionby dissolving in 200 ml of boiling toluene
  5. customA small amount of a high-melting by-product crystallized out at 0° C
  6. filtrationwas filtered off
  7. concentrationOn concentration
  8. customon a rotary evaporator
  9. waitthe mother liquor left 21.1 g (70%) of a pale oil which
  10. customcrystallized after trituration with a little methanol

Sources & evidence

ORD record
ord-25fd7b8e4b9844cfb99183d53529aa68
Source dataset
uspto-grants-1977_11
Patent number
US04057417

Reaction notes

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