Dimethylformamide dimethyl acetal → HCID 54488937, compound

HRID 2352559Notes

Reaction equation

HRID 2352559 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][CH3:9])[N:4]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>>[CH3:12][N:13]([CH3:15])[CH:14]=[N:1][C:2]([C:3]1[O:7][N:6]=[C:5]([CH2:8][CH3:9])[N:4]=1)=[CH:12][N:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 10820904(3-ethyl-1,2,4-oxadiazol-5-yl)methanamine

Product 1

HCID 54488937HCID 54488937, compoundYield 72%

Conditions

Temperature
80 °C

Procedure

A mixture of 11.5 g of 5-aminomethyl-3-ethyl-1,2,4-oxadiazole and 24 ml of dimethylformamide dimethylacetal is heated to 80° C. for 7 hours; during this process, 10 ml of thus-formed methanol is removed by distillation. After adding another 12 ml of DMF-acetal, the mixture is refluxed for 3 hours, then subjected to fractional distillation. The fraction passing over at 155°-160° C. and 0.03 torr, 1,4-bis(di- methylamino)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-2-aza1,3-butadiene is obtained in a yield of 72% of theory; nD20 1.5908.

Workup

  1. customduring this process, 10 ml of thus-formed methanol is removed by distillation
  2. additionAfter adding another 12 ml of DMF-acetal
  3. temperaturethe mixture is refluxed for 3 hours
  4. distillationsubjected to fractional distillation
  5. custompassing over at 155°-160° C. and 0.03 torr

Sources & evidence

ORD record
ord-e8b07586ba904f5984ca0e0f68f4d348
Source dataset
uspto-grants-1989_10
Patent number
US04877792

Reaction notes

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