6-Cyano-5-fluorobenzo[d]thiazole-2-thiolate potassium salt → 5-Fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile

HRID 1848178Notes

Reaction equation

HRID 1848178 reaction equation
[K+].[C:2]([C:4]1[C:13]([F:14])=[CH:12][C:7]2[N:8]=[C:9]([S-:11])[S:10][C:6]=2[CH:5]=1)#[N:3].[K].S[C:17]1SC2C(N=1)=NC=C(C(OCC)=O)C=2>>[F:14][C:13]1[C:4]([C:2]#[N:3])=[CH:5][C:6]2[S:10][C:9]([S:11][CH3:17])=[N:8][C:7]=2[CH:12]=1

Participants

3

Reactant 2

HCID 1178493076-Cyano-5-fluorobenzo[d]thiazole-2-thiolate potassium saltHCID 178469699HCID 178469699, compound

Product 1

HCID 866811685-Fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile

Procedure

5-Fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile was synthesized as an orange solid (1.2 g, 86%) using a procedure analogous to that described in Step 2 of Example 114, substituting 6-cyano-5-fluorobenzo[d]thiazole-2-thiolate potassium salt from the previous step for ethyl 2-mercaptothiazolo[4,5-b]pyridine-6-carboxylate potassium salt used in Example 114. 1H NMR (300 MHz, DMSO-d6) δ 8.67 (d, J=6.4 Hz, 1H), 8.01 (d, J=10.5 Hz, 1H), 2.84 (s, 3H); LCMS (ESI) m/z 225 (M+H)+.

Sources & evidence

ORD record
ord-87c6367bf4d648d988ae841b7ff7e3f0
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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