Ethyl orthoformate → HCID 19987517, compound

HRID 2072735Notes

Reaction equation

HRID 2072735 reaction equation
[CH:1](OCC)(OCC)[O:2]CC.[NH2:11][C:12]1[N:16]=[C:15]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:21]([F:31])[CH:20]=2)[O:14][N:13]=1>>[CH:1]([NH:11][C:12]1[N:16]=[C:15]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:21]([F:31])[CH:20]=2)[O:14][N:13]=1)=[O:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 19800956HCID 19800956, compound

Product 1

HCID 19987517HCID 19987517, compoundYield 83%

Procedure

To triethyl orthoformate (6 ml) was added 3-amino-5-(2-(2-fluoro-4-biphenylyl)ethyl)-1,2,4-oxadiazole (0.10 g, 0.35 mmol). After the mixture was refluxed for 20 h, the mixture was evaporated under reduced pressure to a residue, which was extracted with chloroform after water was added. The extracts were dried with anhydrous potassium carbonate, and evaporated under reduced pressure to a residue, which was chromatographed to afford 3-formylamino-5-(2-(2-fluoro-4-biphenylyl)ethyl)-1,2,4-oxadiazole (0.091 g, 83% yield): NMR(CDCl3)δ 1.86(d, 3H), 4.40(q, 1H), 7.00-7.65(m, 8H), 9.06(broad, 2H) ppm; IR(nujol) 3275, 1740, 1580 cm-1 ; mass m/e 311 (M+).

Workup

  1. temperatureAfter the mixture was refluxed for 20 h
  2. customthe mixture was evaporated under reduced pressure to a residue, which
  3. extractionwas extracted with chloroform after water
  4. additionwas added
  5. dry with materialThe extracts were dried with anhydrous potassium carbonate
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-dcdd2b86a6c44d4786d679cc189859f1
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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