Formic Acid → HCID 11778604, compound

HRID 728177Notes

Reaction equation

HRID 728177 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH2:11]([NH:13][C:14]1[O:15][C:16]2[CH:22]=[C:21]([CH2:23][CH2:24][C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[CH:20]=[CH:19][C:17]=2[N:18]=1)[CH3:12].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:11]([N:13]([C:14]1[O:15][C:16]2[CH:22]=[C:21]([CH2:23][CH2:24][C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[CH:20]=[CH:19][C:17]=2[N:18]=1)[CH:1]=[O:3])[CH3:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 10467596HCID 10467596, compound

Product 1

HCID 11778604HCID 11778604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of acetic anhydride (1.13 ml) and formic acid (0.45 ml) was stirred at 50° C. for 40 minutes. Tetrahydrofuran (10 ml) and 2-ethylamino-6-[2-(2-furyl)ethyl]benzoxazole (1.02 g) was added thereto and the mixture was stirred at the same temperature for further 6 hours. After cooling, the mixture was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water dried over magnesium sulfate and evaporated in vacuo to give 2-(N-ethylformamido)-6-[2-(2-furyl)ethyl]benzoxazole (1.18 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for further 6 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1afe702fd3b64c6696515b0d2be44360
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

Loading…