Formaldehyde → HCID 178443615, compound

HRID 1654429Notes

Reaction equation

HRID 1654429 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.CN1N=NC2C1=CC=CC=2.[CH2:23]=[O:24].[CH2:25]([CH:27]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:28][NH:29][CH2:30][CH:31]([CH2:36][CH3:37])[CH2:32][CH2:33][CH2:34][CH3:35])[CH3:26]>O.CO>[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:23]=[O:24].[CH2:36]([CH:31]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:30][NH:29][CH2:28][CH:27]([CH2:25][CH3:26])[CH2:38][CH2:39][CH2:40][CH3:41])[CH3:37]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 7791Bis(2-ethylhexyl)amineHCID 259021-MethylbenzotriazoleHCID 178424185HCID 178424185, compound

Product 1

HCID 178443615HCID 178443615, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Approximately 40.0 gm (0.3 mole) of tolyltriazole (commercially obtained from PMC Specialties Group, Inc. under the tradename Cobratec TT-100), 25.1 gm (0.31 mole) aqueous formaldehyde (37 wt. % solution in water), and 50 ml of methanol were charged into a 500 ml reactor equipped with a reflux condenser, thermometer, dropping funnel, and mechanical stirrer. The reaction mixture became homogeneous after stirring for about 5 minutes. Then 72.5 gm (0.3 mole) of bis(2-ethylhexyl)amine was slowly added to the reactor at a temperature less than 40° C. (moderate exotherm is observable). Thereafter, the mixture was heated to - 70° C. and maintained at reflux for 3 hrs. Then the reactants were heated at 110° C. during which methanol and water was azeotropically collected in the Dean-Stark trap. Finally, house vacuum was used to remove the trace amount of water at 110° C. for a half hour. A final filtration to remove possible unreacted tolyltriazole is optional. Small amounts of residual water could make the final product appear hazy. Approximately 115.3 gm of yellow liquid was recovered as desired product (>99% yield).

Workup

  1. customequipped with a reflux condenser
  2. temperaturemaintained
  3. temperatureat reflux for 3 hrs
  4. customwas azeotropically collected in the Dean-Stark trap
  5. customto remove the trace amount of water at 110° C. for a half hour
  6. filtrationA final filtration
  7. customto remove possible unreacted tolyltriazole

Sources & evidence

ORD record
ord-84a70a44faee4abbbde8ddee8b03a514
Source dataset
uspto-grants-1995_04
Patent number
US05407592

Reaction notes

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