2-Iodoaniline → 2-(Methoxymethyl)-1,3-benzothiazole

Participants

Role	Name	HCID	Charge
Reactant	2-Iodoaniline	HCID 11995	—
Reactant	Calciumoxide	HCID 6850728	—
Reactant	2-Methoxyethanethioamide	HCID 20323369	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(Methoxymethyl)-1,3-benzothiazole	HCID 4064524	61.2%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 2-iodoaniline (5 g, 22.8 mmol), 2-methoxy-thioacetamide (2.4 g, 22.8 mmol), calcium oxide (1.28 g, 22.8 mmol), tris(dibenzylideneacetone)dipalladium-chloroform adduct (104 mg, 0.114 mmol), diphenylphosphinoferrocine (253 mg, 0.456 mmol) and DMF (23 mL) was stirred at 60° C. for 2 h under nitrogen. The resulting mixture was purified by column chromatography (10 to 20% ethyl acetate:hexanes) to afford 2.5 g (61%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.01-7.9 (m, 1H), 7.98-7.89 (m, 1H), 7.50-7.45 (m, 1H), 7.41-7.38 (m, 1H), 4.86 (s, 2H), 3.54 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08378104B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-d37937e03e974e92820169058727d586
Source note	uspto-grants-2013_02