Ethanol → HCID 178518070, compound

HRID 2063514Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:12][C:13]1C(Cl)=N[CH:16]=[N:17][C:18]=1Cl)=O.N[C:22]([NH2:24])=[S:23].CC[OH:27]>C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[S:23][C:22]2[N:24]=[CH:16][N:17]=[C:18]([OH:27])[C:13]=2[N:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2-(2,6-dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide (77.0 g, 221 mmol), thiourea (16.8 g, 221 mmol), and EtOH (500 mL) was added formic acid (3 mL) at rt. The resulting mixture was heated to 90° C. After 12 h, the reaction mixture was cooled and concentrated. The resulting residue was collected by filtration and washed with H2O (100 mL) followed by hexanes (100 mL). The title compound as a dark brown solid was further dried by high vaccum for 12 h and used crude (68 g, 70% apparent purity by analytical HPLC). An analytically pure sample could be obtained by purified by preparative reverse-phase HPLC to afford the title compound as a colorless solid. MS (ESI): mass calcd. for C12H7Cl2N3OS, 310.9; m/z found, 312.0 [M+H]+. 1H NMR (CD3OD): 8.04 (s, 1H), 7.44-7.37 (m, 2H), 7.31-7.26 (m, 1H), 4.70 (s, 2H).

Workup

temperaturethe reaction mixture was cooled
concentrationconcentrated
filtrationThe resulting residue was collected by filtration
washwashed with H2O (100 mL)
dry with materialThe title compound as a dark brown solid was further dried by high vaccum for 12 h
customAn analytically pure sample could be obtained
customby purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-d938e55b36fc46b9ac0640ac945ee78b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288397B2

Reaction notes

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