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

HRID 389572Notes

Reaction equation

HRID 389572 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][O:10][CH2:11][C:12](N)=[S:13].[O-2].[Ca+2]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].CN(C=O)C>[CH3:9][O:10][CH2:11][C:12]1[S:13][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1

Participants

6

Reactant 3

HCID 119952-IodoanilineHCID 6850728CalciumoxideHCID 203233692-Methoxyethanethioamide

Product 1

HCID 40645242-(Methoxymethyl)-1,3-benzothiazoleYield 61.2%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  1. customThe resulting mixture was purified by column chromatography (10 to 20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-d37937e03e974e92820169058727d586
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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