Methanesulfonic Acid → Di(6-aminohexyl) 3,3'-dithiodipropionate

HRID 1253399

Reaction equation

CS(O)(=O)=O.[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[C:14]([OH:25])(=O)[CH2:15][CH2:16][S:17][S:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>C(C(C)=O)C(C)C>[C:21]([O:23][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH2:6])(=[O:22])[CH2:20][CH2:19][S:18][S:17][CH2:16][CH2:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH2:6])=[O:25]

Participants

Conditions

Temperature: 120 °C

Procedure

2.0 g of methanesulfonic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise, under an atmosphere of nitrogen and at 70° C., to 2.3 g of 6-amino-1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.). After stirring for 10 minutes, 2.1 g of 3,3′-dithiodipropionic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the resulting mixture was heated to 120° C. and then stirred at 110° C. for 3 hours. Following completion of the reaction, the reaction mixture was cooled to room temperature and then added gradually to 50 mL of methyl isobutyl ketone (manufactured by Wako Pure Chemical Industries, Ltd.). After stirring for 2 hours, the precipitated crystals were collected by vacuum filtration and washed with acetone, yielding the methanesulfonate salt of di(6-aminohexyl) 3,3′-dithiodipropionate.

Workup

stirringstirred at 110° C. for 3 hours
customcompletion of the reaction
temperaturethe reaction mixture was cooled to room temperature
stirringAfter stirring for 2 hours
filtrationthe precipitated crystals were collected by vacuum filtration
washwashed with acetone

Sources & evidence

ORD record: ord-5032cbba7aaf45d4a4653b80204863c5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455413B2

Linked notes

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