Ethyl isocyanate → N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9103

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2-Amino-1,3-benzothiazole-6-carbonitrile (0.2 g) was dissolved in about 5 mL dimethylformamide. About 0.2 mL of ethylisocyanate was added, followed by about 0.3 mL triethylamine and the solution was heated to about 80° C. under good agitation. The solution was allowed to stir for about 4 hours then cooled to room temperature. The solvent was removed in vacuo and the solids were washed well with ether. The product was further purified by column chromatography and after drying in vacuo, about 0.14 grams was isolated. 1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes.

Workup

temperaturethen cooled to room temperature
customThe solvent was removed in vacuo
washthe solids were washed well with ether
customThe product was further purified by column chromatography
customafter drying in vacuo
customabout 0.14 grams was isolated
custom1H NMR 1.1 (t, 3H, J=7.2 Hz), 3.2 (m, 2H), 6.8 (s, 1H), 7.7 (m, 2H), 8.4 (s, 1H), 11.0 (s, 1H), LC/MS 2.54 min, 247 (MH+), 245 (M−H−), lab RP-HPLC RT 7.8 minutes

Sources & evidence

ORD record: ord-4bb201544c5043cd978fe2b16f5062ab
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Linked notes

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