Dimethyl Sulfate → 6-methylthiobenz(CD)indol-2-thiol

HRID 1090247Notes

Reaction equation

HRID 1090247 reaction equation
S(OC)(OC)(=O)=O.[CH3:8][S:9][C:10]1[C:11]2[C:12]3[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=O)[C:13]=3[CH:20]=[CH:21][CH:22]=2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>N1C=CC=CC=1>[CH3:8][S:9][C:10]1[C:11]2[C:12]3[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([SH:24])[C:13]=3[CH:20]=[CH:21][CH:22]=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14817Phosphorus sulfide (P2S5)HCID 197508246-(Methylthio)benz[cd]indol-2(1H)-one

Product 1

HCID 1785030816-methylthiobenz(CD)indol-2-thiol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Chlorosulfonation of benz(cd)indol-2-(1H-one yields the 6-sulfonylchloride derivative, which upon treatment with zinc dust in acetic acid-hydrochloric acid solution, yields 6-mercaptobenz(cd)indol-2-(1H)-one. Treatment with dimethyl sulfate in alkaline solution leads to 6-methylthiobenz(cd)indol-2-(1H)-one, which on heating with P2S5 in pyridine yields 6-methylthiobenz(CD)indol-2-thiol. The reaction of the latter compound with molar equivalents of 3-(4-pyridinyl)propanamine and mercuric acetate in ethanol, under the conditions of Example 55, leads to the title compound.

Sources & evidence

ORD record
ord-194c1291914b4ffdbbb2b91699dec300
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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