Oleylmethyldihydroxyethylammonium chloride → Di(oleylmethyldihydroxyethylammonium) cystinate

HRID 1461638Notes

Reaction equation

HRID 1461638 reaction equation
[Cl-].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[K+].[CH2:27]([S:33][S:34][CH2:35][C@H:36]([NH2:40])[C:37]([O-:39])=[O:38])[C@H:28]([NH2:32])[C:29]([O-:31])=[O:30].[K+]>C(O)(C)C>[CH2:27]([S:33][S:34][CH2:35][C@H:36]([NH2:40])[C:37]([O-:39])=[O:38])[C@H:28]([NH2:32])[C:29]([O-:31])=[O:30].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 86745345Oleylmethyldihydroxyethylammonium chlorideHCID 131717134Cystine potassium salt

Product 1

HCID 131717133Di(oleylmethyldihydroxyethylammonium) cystinateYield 98.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 81 g of oleylmethyldihydroxyethylammonium chloride, 33 g of cystine potassium salt and 200 g of isopropyl alcohol and the reaction was conducted at 65°-75° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 7 hours. The precipitate was then filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in 200 g of toluene and the insolubles were filtered off. Finally, the filtrate was concentrated to give 95.2 g (theoretical yield 97.8 g) of di(oleylmethyldihydroxyethylammonium) cystinate as a waxy product.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 65°-75° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 7 hours
  4. filtrationThe precipitate was then filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 200 g of toluene
  7. filtrationthe insolubles were filtered off
  8. concentrationFinally, the filtrate was concentrated

Sources & evidence

ORD record
ord-071338475a114e8e80a05352fab40f67
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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