Hydrochloric Acid → HCID 42878057, compound

HRID 18115Notes

Reaction equation

[O:1]=[S:2]1(=[O:16])[C:13]2[C:5](=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9]C(=O)[C:7]3=[O:15])[CH2:4][CH2:3]1.[OH-:17].[Na+].OO.Cl>O>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[S:2](=[O:1])(=[O:16])[CH2:3][CH2:4][C:5]=2[C:6]=1[C:7]([OH:15])=[O:17]

Participants

Conditions

Temperature: 40 °C

Procedure

1.5 g (6.32 mmol) of 3,3-dioxo-1,2,3,6-tetrahydro-3λ6-thieno[3,2-e]indole-7,8-dione were introduced into a 10 ml three-neck round-bottom flask and dissolved in 6.5 ml of 1M (207.2 mmol) sodium hydroxide solution. 1.5 ml (1.32 mmol) of a 30% strength hydrogen peroxide solution were slowly added dropwise over the course of 30 minutes. The internal temperature during the addition was kept between 30-40° C. despite the exothermic reaction. After the addition was complete, the mixture was stirred at 40° C. for 1.5 h. The mixture was then cooled to RT and, after addition to a little water (about 7 ml), acidified with a 10% strength HCl to pH 1, and the precipitated solid was filtered off with suction. The latter was washed successively with water and diethyl ether and dried in vacuo overnight. 870 mg of the desired compound were obtained.

Workup

additionThe internal temperature during the addition
customwas kept between 30-40° C. despite the exothermic reaction
additionAfter the addition
temperatureThe mixture was then cooled to RT
filtrationthe precipitated solid was filtered off with suction
washThe latter was washed successively with water and diethyl ether
customdried in vacuo overnight

Sources & evidence

ORD record: ord-cc35f39e22f0468dbd1d3986ce7c4cdd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741333B2

Reaction notes

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