Ammonia → HCID 69157470, compound

HRID 1376282Notes

Reaction equation

HRID 1376282 reaction equation
[ClH:1].C(O[C:5](=[NH:15])/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)C.[NH3:16]>CO>[ClH:1].[F:14][C:11]1[CH:10]=[CH:9][C:8](/[CH:7]=[CH:6]/[C:5]([NH2:15])=[NH:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69158140HCID 69158140, compound

Product 1

HCID 69157470HCID 69157470, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of E-3-(4-fluorophenyl)acrylirnidic acid ethyl ester hyrochloride (0.86 g, 0.00374 moles) in dry methanol (20 ml) was treated with a solution of ammonia (0.064 g, 3.8 mmol) in dry methanol (0.51 ml) and the resulting solution was allowed to stand at room temperature for 48 h. The reaction mixture was evaporated to dryness, mixed with diethyl ether and evaporated to give E-3-(4-fluorophenyl)acrylamidine hydrochloride as a solid (0.75 g, 100%); 1H-NMR (d6-DMSO) 6.72, 6.79 (1H, d) 7.35 (2H, m), 7.67 (2H, m), 7.87, 7.94 (1H, d), 8.8, 9.15 (2×bs). MS (APCl+)M+1=165, C9H9FN2 requires 164.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionmixed with diethyl ether
  3. customevaporated

Sources & evidence

ORD record
ord-90881a82c7354619a867793d47589c38
Source dataset
uspto-grants-2007_01
Patent number
US07169924B2

Reaction notes

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