Hydrochloric Acid → 5-Methylbenzo[d]thiazol-2(3H)-one

Reaction equation

C(CC(C)(C)C)(C)C.C([O:12]C(C)C)(C)C.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][CH2:24]C(O)=O)=[C:19]([N+:28]([O-])=O)[CH:18]=1.Cl>>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]2[S:23][C:24](=[O:12])[NH:28][C:19]=2[CH:18]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 12330517HCID 12330517, compound

HCID 88774032HCID 88774032, compound

Product 1

HCID 28015065-Methylbenzo[d]thiazol-2(3H)-oneYield 74%

Procedure

Analogous to Example 2(a), 2-acetyl-5-methyl-2-(3H)-benzothiazolone, m.p. 86°-88° C. (from isooctane/diisopropyl ether), was prepared with a yield of 51% of theory, starting from [(4-methyl-2-nitrophenyl)thio]-acetic acid. This intermediate was subsequently treated with 5 N hydrochloric acid analogous to Example 2(b). 5-Methyl-2(3H)-benzothiazolone was obtained with a yield of 74% of theory; m.p. 178°-180° C. (from ethanol/water 1:1).

Sources & evidence

ORD record: ord-0f32851efd544657814063c8434d6535
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04353919

Reaction notes

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