Ethyl isocyanate → 1-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

HRID 712151Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH:17][C:23]([NH:22][CH2:20][CH3:21])=[O:24])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 82.5 °C

Procedure

To asuspension of 5-benzyloxy-7-bromo-1,3-benzothiazol-2-amine (216 g, 0.64 mol) in 1,4-dioxane (4 L) was added ethylisocyanate (380 mL, 4.81 mol). The reaction mixture was heated to 80-85° C. overnight. After completion of reaction (by TLC) 1,4-dioxane was distilled off and the residue was co-evaporated with hexane. The residue was treated with water at 78-80° C. for 3-5 h. The resulting solid was filtered off and again washed with hot water, dried under high vacuum to obtain an off-white solid that was washed with hexane to obtain the desired product (196 g, 75%). 1H-NMR (DMSO-d6): δ 1.08 (t, J=7.20 Hz, 3H), 3.18 (q, J=6.80 Hz, 2H), 5.17 (s, 2H), 6.71 (br s, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.26 (br s, 1H), 7.31-7.47 (m, 5H) and 10.82 (br s, 1H). LCMS: 405.90 [M+H]+.

Workup

distillationwas distilled off
additionThe residue was treated with water at 78-80° C. for 3-5 h
filtrationThe resulting solid was filtered off
washagain washed with hot water
customdried under high vacuum
customto obtain an off-white solid
washthat was washed with hexane

Sources & evidence

ORD record: ord-89370ad09a924782996f78ab1298c30e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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