Ammonia → 5-Methoxy-2-nitro-thioxanthene-9-one

HRID 1825780Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:11]=1[C:12]([OH:14])=O.N>CS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[S:9][C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:11]=1[C:12]2=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(2-Methoxy-phenylsulfanyl)-5-nitro-benzoic acid (13.00 g, 42.58 mmol) was suspended in methanesulphonic acid (100 ml) and heated at 100° C. The crude mixture was slowly poured onto ice with vigorous stirring then neutralized with conc. ammonia solution. The precipitate was filtered and washed with water. The yellow/lime colored solid was dried under vacuum at 50° C. to give the crude title compound which was used without any further purification (12 g, 98%). m/z (LC-MS, ESP), RT=4.89 min, (M++1)=288.

Workup

filtrationThe precipitate was filtered
washwashed with water
dry with materialThe yellow/lime colored solid was dried under vacuum at 50° C.

Sources & evidence

ORD record: ord-94f0db9258864343b02950bd38c5158e
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049313B2

Reaction notes

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