Sodium ethoxide → HCID 178479326, compound

HRID 1824019Notes

Reaction equation

HRID 1824019 reaction equation
[O-]CC.[Na+].Cl.[CH2:6]([NH:13][C:14]([NH2:16])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[CH2:25][C:26](OC)=[O:27]>>[ClH:17].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[CH2:25][C:26]([NH:15][C:14]([NH:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[NH:16])=[O:27]

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 2734107Methyl 2,6-dichlorophenylacetateHCID 1784794191-Benzylguanidine hydrochloride

Product 1

HCID 178479326HCID 178479326, compoundYield 128%

Procedure

To sodium ethoxide [prepared by reacting sodium (60 mg, 2.61 mmol) and anhydrous ethanol (5 ml)] benzylguanidine hydrochloride (580 mg, 3.12 mmol) was added and refluxed in an oilbath for 1 hour. The reaction mixture was cooled to room temperature and insoluble materials filtered. Methyl 2,6-dichlorophenylacetate (285 mg, 1.3 mmol) (CH3(C═O)CH2(2,6,-di-ClC6H3) was added to the filtrate and refluxed for 2 hours. After cooling to room temperature the reaction mixture was concentrated and converted to the hydrochloride salt by the addition of hydrogen chloride (1M in ether) to provide 310 mg of N-(2,6-dichlorophenylacetyl)-N′-benzylguanidine hydrochloride as a white solid, purity 89.3% (HPLC); 1H-NMR (CD3OD) δ 4.38 (s, 4H, CH2), 7.32–7.41 (m, 8H, Ar).

Workup

  1. temperaturerefluxed in an oilbath for 1 hour
  2. filtrationinsoluble materials filtered
  3. temperaturerefluxed for 2 hours
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. concentrationwas concentrated
  6. additionconverted to the hydrochloride salt by the addition of hydrogen chloride (1M in ether)

Sources & evidence

ORD record
ord-abe5d670ec87442188c3d791a686808c
Source dataset
uspto-grants-2006_05
Patent number
US07041702B1

Reaction notes

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