Hydrochloric Acid → HCID 178492759, compound

HRID 1902568Notes

Reaction equation

[CH3:1][O-:2].[Na+].CO.[C:6]1([CH3:33])[CH:11]=[CH:10][C:9]([N:12]=[C:13]([OH:32])[C:14]2[C:15](=[CH:19][C:20]([N+]([O-])=O)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([OH:18])=[S:17])=[CH:8][CH:7]=1.Cl>CS(C)=O>[C:6]1([CH3:33])[CH:11]=[CH:10][C:9]([N:12]=[C:13]([OH:32])[C:14]2[C:15](=[CH:19][C:20]([O:2][CH3:1])=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([OH:18])=[S:17])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

110 ml of 1.0 M sodium methylate solution in 110 mmols of absolute methanol are evaporated to dryness and the residue is suspended in 200 ml of dimethyl sulfoxide. 39.04 g (100 mmols) of 5-nitro-3-phenylthiophthalic acid N-p-toluylimide in 200 ml of dimethyl sulfoxide are added, the mixture is stirred for one day at 25° C. and then discharged into 1.5 liters of dilute hydrochloric acid and the resulting mixture is extracted with chloroform. The organic phase is washed three times with water, dried over sodium sulfate and evaporated. After recrystallisation from toluene/cyclohexane, 31.68 g (84% of theory) of the title imide, with a melting point of 166°-168° C., are obtained.

Workup

extractionthe resulting mixture is extracted with chloroform
washThe organic phase is washed three times with water
dry with materialdried over sodium sulfate
customevaporated
customAfter recrystallisation from toluene/cyclohexane, 31.68 g (84% of theory) of the title imide
customwith a melting point of 166°-168° C., are obtained

Sources & evidence

ORD record: ord-33f1237fcdec4d7fa5519c7a7f5e1770
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363917

Reaction notes

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