Formaldehyde → HCID 178449032, compound

HRID 1654430Notes

Reaction equation

HRID 1654430 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][NH:10][CH:11]=1.[CH2:13]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]([CH3:16])[CH3:15].[CH2:22]=[O:23]>CC(O)C>[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][N:9]=[N:10][C:11]=1[CH:22]=[O:23].[CH2:13]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8085DiisobutylamineHCID 178424185HCID 178424185, compound

Product 1

HCID 178449032HCID 178449032, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

Approximately 80.1 gm (0.6 mole) of tolyltriazole, 200 ml 2-propanol, and 78.0 gm (0.6 mole) diisobutylamine were mixed in a 500 ml reactor until a homogeneous phase was formed. 51.0 gm (0.618 mole) of aqueous formaldehyde was slowly added while maintaining a reactor temperature ≤40° C. Thereafter, the reactants were heated at 82±2° C. for 4 hrs., then at 110±2° C. for two additional hours during which isopropanol and water were removed by distillation. The final product (163.5 gm) is a yellowish liquid which solidifies upon standing at ambient temperature (m.p. 49°-51° C.). A final filtration to remove possibly unreacted tolyltriazole is optional. However, small amounts of residual water could make the final product appear hazy.

Workup

  1. customwas formed
  2. temperaturewhile maintaining a reactor temperature ≤40° C
  3. custom, then at 110±2° C. for two additional hours during which isopropanol and water were removed by distillation
  4. customupon standing at ambient temperature
  5. filtrationA final filtration
  6. customto remove possibly unreacted tolyltriazole

Sources & evidence

ORD record
ord-9bd2ee60972547c293e5de42bcb94d90
Source dataset
uspto-grants-1995_04
Patent number
US05407592

Reaction notes

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