Sodium Hydroxide → N,N'-(disulfanediyldiethane-2,1-diyl)bis(4-chlorobutanamide)

HRID 2425818Notes

Reaction equation

HRID 2425818 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][S:5][S:6][CH2:7][CH2:8][NH2:9].[OH-:10].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>C1COCC1>[S:5]([CH2:4][CH2:3][NH:2][C:13](=[O:10])[CH2:14][CH2:15][CH2:16][Cl:1])[S:6][CH2:7][CH2:8][NH:9][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][Cl:12]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 783704-Chlorobutyryl chlorideHCID 1676282-[(2-Aminoethyl)disulfanyl]ethan-1-amine hydrochloride

Product 1

HCID 10666287N,N'-(disulfanediyldiethane-2,1-diyl)bis(4-chlorobutanamide)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

60 g of cystamine hydrochloride are solubilized in 500 mL and cooled to 5° C. pH is raised to 10 by addition of aq. NaOH (30%). A solution of 4-chlorobutanoyl chloride (105 g) in anhydrous THF (500 mL), is added dropwise, while pH is maintained above 7 by addition of aq. NaOH (30%). After completion of the addition and stabilization of pH at 7, the mixture is kept mixing for 3 d. The aqueous layer is extracted with 3×500 mL dichloromethane, combined with THF layer and dried over Na2SO4. After drying under vacuum, 41 g of a white powder are collected. Analyses are in accordance with the expected structure.

Workup

  1. additionAfter completion of the addition and stabilization of pH at 7
  2. additionthe mixture is kept mixing for 3 d
  3. extractionThe aqueous layer is extracted with 3×500 mL dichloromethane
  4. dry with materialdried over Na2SO4
  5. dry with materialAfter drying under vacuum, 41 g of a white powder
  6. customare collected

Sources & evidence

ORD record
ord-c3726e6f972847dcb5cd39669cdb6322
Source dataset
uspto-grants-2011_06
Patent number
US07967872B2

Reaction notes

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