Triethylamine → HCID 10370874, compound

HRID 2392688Notes

Reaction equation

HRID 2392688 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1.[C:23](Cl)(=O)[C:24](Cl)=O.[CH3:29][O:30][C:31]1[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[CH:36][C:32]=1NC=O.[CH2:43]([N:45]([CH2:48]C)[CH2:46]C)C>ClCCl.CN(C=O)C>[CH3:43][N:45]([CH3:48])[CH2:46][CH2:23][CH2:24][C:32]1[CH:36]=[C:37]([NH:40][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:3]3[CH:4]=[CH:5][C:6]([C:8]4[N:12]=[C:11]([CH3:13])[O:10][N:9]=4)=[CH:7][C:2]=3[CH3:1])=[CH:19][CH:18]=2)=[O:22])[CH:38]=[CH:39][C:31]=1[O:30][CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 264510N-(2-methoxy-5-nitrophenyl)formamideHCID 111301684-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic Acid

Product 1

HCID 10370874HCID 10370874, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (E. P. 0533268A 1) (0.212 g, 0.721 mmol) was suspended in dichloromethane (5 ml) and treated with oxalyl chloride (0.094 ml, 1.08 mmol), followed by a drop of dry DMF with stirring. After 4 h, the reaction mixture was evaporated under reduced pressure and dried in vacuo to give the crude acid chloride as a yellow solid. Meanwhile to a solution of the product from description 2 (0.142 g, 0.683 mmol) in dichloromethane (10 ml); triethylamine (0.095 ml, 0.683 mmol) was added, followed by a solution of the crude acid chloride in dichloromethane (4 ml), with stirring. After 1 h, the reaction mixture was washed with water (1×), followed by sodium bicarbonate solution (1×). The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a brown oil which was dried in vacuo. The oil was purified by SiO2 chromatography (7.5% MeOH in CH2Cl2 as eluant) to give the title compound as a pale yellow oil (0.052 g, 16%) which was converted to its oxalate salt. m.pt 144°-148° C. (oxalate salt)

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customdried in vacuo
  3. customto give the crude acid chloride as a yellow solid
  4. stirringwith stirring
  5. waitAfter 1 h
  6. washthe reaction mixture was washed with water (1×)
  7. dry with materialThe organic layer was then dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customto give a brown oil which
  10. customwas dried in vacuo
  11. customThe oil was purified by SiO2 chromatography (7.5% MeOH in CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-3a6a830cc81f4173865e64339a8c71f9
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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