1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59350294, compound

HRID 2271392Notes

Reaction equation

HRID 2271392 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:25]([OH:27])=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:30]=1[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:25]([O:27][C:12]1[CH:13]=[CH:2][CH:3]=[C:4]([C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[CH:11]=1)=[O:26])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111339693,4,5-Tris(benzyloxy)benzoic AcidHCID 13137382Allyl 3-hydroxybenzoate

Product 1

HCID 59350294HCID 59350294, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl 3-hydroxybenzoate (2.82 g, 15.8 mmol), 3,4,5-tribenzyloxybenzoic acid (10.7 g, 23.1 mmol), DMAP (5.51 g, 26.5 mmol), and CH2Cl2 (200 mL) were combined and stirred under a nitrogen atmosphere. EDC.HCl (5.51 g, 28.8 mmol) was added to the mixture and the reaction was allowed to reflux overnight under a nitrogen atmosphere. The reaction was then extracted with 5% citric acid (2×), saturated aqueous sodium bicarbonate (2×), and brine (1×), dried over MgSO4, filtered, and concentrated in vacuo to obtain a solid (9.46 g, 99%) that was used without further purification.

Workup

  1. temperatureto reflux overnight under a nitrogen atmosphere
  2. extractionThe reaction was then extracted with 5% citric acid (2×), saturated aqueous sodium bicarbonate (2×), and brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8296be7bec9643fb82d8e44d6b1c5df4
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

Loading…