Pyridine → Ethyl 4-methyl-5-(4-nitrophenyl)-2-(3-phenylureido)thiophene-3-carboxylate

HRID 23252Notes

Reaction equation

N1C=CC=CC=1.[C:7]1([N:13]=[C:14]=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:16][C:17]1[S:18][C:19]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[C:20]([CH3:27])[C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[CH3:27][C:20]1[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([NH:16][C:14]([NH:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:15])[S:18][C:19]=1[C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 97.5 °C

Procedure

Toluene (500 ml), pyridine (12.27 g, 155.06 mmol) and phenyl isocyanate (14.58 g, 122.41 mmol) were added to ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate (25.00 g, 81.61 mmol), and the mixture was stirred at 95-100° C. for 4 hours. It was confirmed that starting materials were almost disappeared. After the reaction solution was stirred for 2 hours under ice-cooling, the crystals were isolated with a centrifuging machine and washed with cold toluene (150 ml). The crystals were dried under vacuum at 60° C. for 8 hours to give ethyl 4-methyl-5-(4-nitrophenyl)-2-(3-phenylureido)thiophene-3-carboxylate (32.42 g, 76.20 mmol, 93.4%)

Workup

stirringAfter the reaction solution was stirred for 2 hours under ice-
temperaturecooling
customthe crystals were isolated with a centrifuging machine
washwashed with cold toluene (150 ml)
customThe crystals were dried under vacuum at 60° C. for 8 hours

Sources & evidence

ORD record: ord-6ad1798a0b594bf49f4b78333436ad74
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849738B2

Reaction notes

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