Formic Acid → Diisopropyl Ether

HRID 1902871Notes

Reaction equation

HRID 1902871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][N:11]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[C:23](O[C:27](=[O:29])[CH3:28])(=[O:25])C.[CH:30](O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH:10]1[N:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:13][N:14]1[CH:23]=[O:25].[CH:27]([O:29][CH:22]([CH3:21])[CH3:17])([CH3:30])[CH3:28]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 178478126HCID 178478126, compound

Product 2

HCID 7914Diisopropyl EtherHCID 20513875HCID 20513875, compound

Procedure

2.3 g of 2-([{2-[(2,5-dichlorophenyl)-imino]-1-imidazolidinyl}oxy]methyl)pyridine and 5.1 ml of formic acid are cooled to 5° and treated with 12.2 ml of acetic acid anhydride. The solution is warmed to room temperature and evaporated in vacuo. The residue is taken up in ether. The organic phase is washed with a saturated sodium bicarbonate solution, dried and evaporated in vacuo. The residual of oil is chromatographed on silica gel with a mixture of 4 parts of chloroform and 1 part of ethyl acetate as the elution agent. There is obtained crystalline 2-[(2,5-dichlorophenyl)amino]-1-formyl-3-(2-pyridylmethoxy)imidazolidine of melting point 91°-92° (isopropyl ether).

Workup

  1. customevaporated in vacuo
  2. washThe organic phase is washed with a saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated in vacuo
  5. customThe residual of oil is chromatographed on silica gel with a mixture of 4 parts of chloroform and 1 part of ethyl acetate as the elution agent

Sources & evidence

ORD record
ord-f5797b5117af4dd3b2c5917f5fa5c4b8
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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