Phosphorus oxychloride → HCID 43805572, compound
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([Cl:11])[CH:3]=1.[NH:12]([C:14](=[S:16])[NH2:15])[NH2:13].P(Cl)(Cl)(Cl)=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:16][C:14]([NH2:15])=[N:12][N:13]=2)=[C:4]([Cl:11])[CH:3]=1Participants
Conditions
- Temperature
- 78 °C
Procedure
To an ice cooled mixture of 4-bromo-2-chlorobenzoic acid (2 g, 8.49 mmol) and hydrazinecarbothioamide (1.161 g, 12.74 mmol) was added phosphorous oxychloride (2.375 mL, 25.5 mmol) slowly, and the reaction was heated at 78° C. for 3 hours. After cooling to 0° C., ice water was added and the mixture was vigorously stirred for 1 hour. The resulting precipitate was filtered, washed with water then re-suspended in saturated NaHCO3(aq) and water (1:1) and stirred for 1 hour. The solid was filtered, washed with water, and dried in vacuo to afford the title compound which was used without further purification (2 g, 81% yield). MS m/z 291.9 [M+H]+, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80-8.09 (m, 2H), 7.68 (dd, J=2.02, 8.59 Hz, 1H), 7.55 (br. s, 2H).
Workup
- temperatureAfter cooling to 0° C.
- filtrationThe resulting precipitate was filtered
- washwashed with water
- stirringwater (1:1) and stirred for 1 hour
- filtrationThe solid was filtered
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-5e8284f21f0f47e68674d3f7ef79682f
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040712B2
Reaction notes
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