Triethylamine → HCID 178513054, compound

HRID 1833417Notes

Reaction equation

HRID 1833417 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14](=[NH:18])OCC)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:26]([NH:28][NH2:29])=[O:27]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]([NH:29][NH:28][CH:26]=[O:27])=[NH:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 21389354HCID 21389354, compound

Product 1

HCID 178513054HCID 178513054, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 120 g (0.42 mole) of ethyl 5-(4-chlorophenyl)-2-furimidate hydrochloride in 700 ml of absolute ethanol was added dropwise 62 ml (0.46 mole) of triethylamine at a temperature of 2°-4° while under a nitrogen atmosphere. To this stirring mixture was added portionwise 28 g (0.47 mole) of formic acid hydrazide while maintaining the temperature at 4°-7° by means of an ice bath. The mixture was kept at 5°-7° for 15 minutes, allowed to warm to 23° over a 21/2 hour period, cooled to 10°, filtered, and washed in stirring S.D.A #32 to yield 52 g (47%). An analytical sample was prepared by drying a sample in a vacuum pistol with refluxing chloroform, m.p. 155°-157° (Mel-Temp).

Workup

  1. temperaturewhile maintaining the temperature at 4°-7° by means of an ice bath
  2. temperatureto warm to 23° over a 21/2 hour period
  3. temperaturecooled to 10°
  4. filtrationfiltered
  5. washwashed
  6. customto yield 52 g (47%)
  7. customAn analytical sample was prepared
  8. dry with materialby drying a sample in a vacuum pistol with refluxing chloroform, m.p. 155°-157° (Mel-Temp)

Sources & evidence

ORD record
ord-635c12bedd2e4bdcb84823dc118cfbc7
Source dataset
uspto-grants-1978_01
Patent number
US04066668

Reaction notes

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