Ethyl isocyanate → 1-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 2068704Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15]>O1CCOCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:17]([NH:16][CH2:14][CH3:15])=[O:18])=[N:7][C:6]=2[CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-bromo-6-methoxybenzo[d]thiazol-2-amine V (2.0 g, 7.72 mmol) in 1,4-dioxane (20.0 mL) was added ethylisocyanate (3.0 mL, 38.60 mmol) and heated the resulting reaction mixture to 80° C. for 16 h. After the completion of the reaction (TLC monitoring), 1,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 90° C. for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (2.10 g, 83%). 1H NMR (400 MHz, DMSO-d6): δ 1.07 (t, J=7.20 Hz, 3H), 3.17 (quintet, J=6.80 Hz, 2H), 3.86 (s, 3H), 6.65 (br s, 1H), 7.68 (s, 1H), 7.80 (s, 1H) and 10.67 (br s, 1H). MS: 330.08 (M+H)+.

Workup

temperatureheated
customthe resulting reaction mixture to 80° C. for 16 h
distillationwas distilled off
filtrationfollowed by filtration

Sources & evidence

ORD record: ord-b184b2b19aba490d87059b6a59098a30
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299065B2

Reaction notes

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