Hydrochloric Acid → hexamethylene bis(thiosulphate)N-tert-butyl-N-benzylammonium salt

HRID 463540

Reaction equation

Cl[CH2:2][CH:3]1CC[CH:6]([CH2:9]Cl)[CH2:5][CH2:4]1.O.O.O.O.O.[S:16]([O-:20])([O-:19])(=[O:18])=[S:17].[Na+].[Na+].[C:23]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:26])([CH3:25])[CH3:24].Cl.[S:36]([O-:40])([O-:39])(=[O:38])=[S:37]>CO.O>[C:23]([NH2+:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:26])([CH3:24])[CH3:25].[S:16]([O-:20])([O:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:9][O:39][S:36]([O-:40])(=[O:38])=[S:37])(=[O:18])=[S:17].[C:23]([NH2+:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 135 °C

Procedure

1,4-bis(chloromethyl)cyclohexane (0.165 mole), sodium thiosulphate pentahydrate (0.369 mole) sodium sulfite (6.1 g), methanol (150 ml) and water (150 ml) were charged into an autoclave and heated at 135° C. for 45 minutes. To the cooled reaction mixture, which was a solution of 1,4-dimethylcyclohexane-α,α-bis(thiosulphate)sodium salt, 400 ml of water was added. N-tert-butylbenzylamine (0.306 mole) in 150 ml methanol and 850 ml H2O was adjusted with concentrated HCl to pH4, and the resulting solution was added with stirring to the thiosulphate solution. The white precipitate was filtered, washed with water and dried. Yield: 92 g, (91%) of 1,4-dimethylcyclohexane-α,α-bis(thiosulphate)N-tert-butyl, N-benzylammonium salt.

Workup

customTo the cooled reaction mixture, which
additionwas added
additionthe resulting solution was added
filtrationThe white precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-32b8be04b6174a2580d656012a7d1254
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04520154

Linked notes

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