Benzoyl isothiocyanate → 1-(((Benzoylamino)thioxomethyl)amino)-1H-pyrrole-2-carboxamide

HRID 1685965Notes

Reaction equation

[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([NH2:20])=[O:19]>CC(C)=O>[C:1]([NH:9][C:10](=[S:11])[NH:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([NH2:20])=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of benzoylisothiocyanate (1.2 mL, 8.8 mmol) in acetone (10 mL) was treated with 1-aminopyrrole-2-carboxamide (1.0 g, 8.0 mmol) at ambient temperature. The resulting suspension was stirred for one hour and then cooled to 0° C. The solid material was collected by vacuum filtration and washed with diethyl ether before drying under high vacuum to afford 1A (2.2 g, 96%). HPLC tR=2.55 min (YMC S5 Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=289.29. 1H NMR (400 MHz, DMSO-d6) δ 12.9 (s, 1H), 11.9 (s, 1H), 8.0 (dd, 2H, J=1.2, 7.2 Hz), 7.68 (t, 1H, J=7.6 Hz), 7.55 (m, 3H), 7.03 (s, 1H), 6.92 (br s, 1H), 6.82 (dd, 1H, J=1.6, 4.0 Hz), 6.11 (dd, 1H, J=3.2, 4.0 Hz).

Workup

filtrationThe solid material was collected by vacuum filtration
washwashed with diethyl ether
custombefore drying under high vacuum

Sources & evidence

ORD record: ord-bf0daa53344d4b7f9838a019796c65e7
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148523B2

Reaction notes

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