4-Chlorobenzene-1-carboximidamide hydrochloride → HCID 12535814, compound

HRID 1777002Notes

Reaction equation

HRID 1777002 reaction equation
[O-][CH2:2]C.[Na+].C(O[CH:8]([C:14]([O:16]CC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C.Cl.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[NH:26])=[CH:23][CH:22]=1>C(O)C>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]2[NH:27][C:14](=[O:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:2][N:26]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 2034364-Chlorobenzene-1-carboximidamide hydrochlorideHCID 2723922Sodium ethoxideHCID 12196926Diethyl ethoxypropanedioate

Product 1

HCID 12535814HCID 12535814, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide (11.12 ml, 2 equiv) as a 21% w/v solution in ethanol was added dropwise to a suspension of diethyl ethoxymalonate (3.03 ml, 1 equiv) and 4-chlorobenzamidine hydrochloride (4.23 g, 1 equiv) in ethanol (30 ml), then the mixture was heated to reflux for 4 hours. After cooling, the solvent was removed in vacuo and the residue was triturated with ether. The solid was filtered off, then resuspended in water and acidified to pH 2. The product was filtered off, washed with water and dried; yield 2.94 g. 1H-NMR (d6-DMSO) δ 1.29 (3H,t), 4.26 (2H,q), 7.65 (2H,m), 8.18 (2H,m), 8.65 (1H,s); MS (APCI−) found (M−1)=277/279; C13H11ClN2O3 requires 278/280.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue was triturated with ether
  6. filtrationThe solid was filtered off
  7. filtrationThe product was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-b3bba7eb772f4fa298f43383ec431159
Source dataset
uspto-grants-2016_02
Patent number
US09266841B2

Reaction notes

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