2,2-Diethoxyethylamine → HCID 178467946, compound

HRID 1656518Notes

Reaction equation

HRID 1656518 reaction equation
Cl.[F:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=[NH:11])OCC)=[CH:5][CH:4]=1.[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18][NH2:19])[CH3:15]>C(O)C>[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18][NH:19][C:7](=[NH:11])[C:6]1[CH:5]=[CH:4][C:3]([F:2])=[CH:13][CH:12]=1)[CH3:15]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 122821594-Fluorobenzimidic acid ethyl ester hydrochloride

Product 1

HCID 178467946HCID 178467946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-fluorobenzimidate hydrochloride (18.5 g) in ethanol (90 mL) at 0° C. was added aminoacetaldehyde diethyl acetal (14.5 mL) and the resulting solution was kept at 5° C. overnight. The solvent was evaporated, the resulting oil was dissolved in 1N sodium hydroxide (200 mL), and the solution was extracted with dichloromethane. The organic extracts were dried and evaporated to yield N-(2,2-diethoxyethyl)-4-fluorobenzamidine as an oil (21 g); MS: m/z=255(M+1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting oil was dissolved in 1N sodium hydroxide (200 mL)
  3. extractionthe solution was extracted with dichloromethane
  4. customThe organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-59f7e61c2cde4d8591621eb3cf94f238
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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