Hydrochloric Acid → HCID 135518082, compound

HRID 1824812Notes

Reaction equation

C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1.Cl.N1C=CC=CC=1.Cl>>[OH:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:19]=[CH:18][C:6]=3[N:7]=2)=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 10016034HCID 10016034, compound

HCID 10176127Pyridinium chloride

Product 1

HCID 135518082HCID 135518082, compoundYield 100%

Procedure

6-Methoxy-2-(4-methoxy-phenyl)-benzothiazole (134 mg, 0.49 mmol) and pyridine hydrochloride (1.34 g, 11.6 mmol) were heated to 200° C. under nitrogen for 40 min, and then cooled to room temp. Reaction was poured cautiously into aqueous hydrochloric acid (1M) and extracted with ethyl acetate. Ethyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine and concentrated in vacuo. Residue was washed with ether/hexane (1:4), dried under vacuum yielding the title compound (119 mg, 100%) as a yellow solid. MH+=244 The starting 6-Methoxy-2-(4-methoxy-phenyl)-benzothiazole was prepared as follows:

Workup

customReaction
extractionextracted with ethyl acetate
washEthyl acetate extracts were washed with: 1) hydrochloric acid (1.0M), 2) saturated brine
concentrationconcentrated in vacuo
washResidue was washed with ether/hexane (1:4)
customdried under vacuum

Sources & evidence

ORD record: ord-e98bcbdd54b24dee92f2a56c1bb7b957
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045539B2

Reaction notes

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