Ethyl isocyanate → 1-Ethyl-3-(7-nitro-5-pyridin-3-yl-benzothiazol-2-yl)-urea

HRID 447022Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred mixture of 7-Nitro-5-pyridin-3-yl-benzothiazol-2-ylamine (100 mg, 0.3676 mmol), ethyl isocyanate (0.18 ml, 1.831 mmol) and dibutyltindiacetate (10 drops) in anhydrous 1,4-dioxane (10 ml) was heated in a sealed vessel at 100° C. for 16 h. After cooling to ambient temperature, the precipitated solid was collected by filtration, washed with 1,4-doxane and dried in vacuo to give 1-Ethyl-3-(7-nitro-5-pyridin-3-yl-benzothiazol-2-yl)-urea as a yellow solid (30 mg, 24%).

Workup

temperatureAfter cooling to ambient temperature
filtrationthe precipitated solid was collected by filtration
washwashed with 1,4-doxane and
customdried in vacuo

Sources & evidence

ORD record: ord-c71f997a6b6a45d6b378d31acb4af72e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481544B2

Reaction notes

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