1,1-Dichloroethane → HCID 11959847, compound
Reaction equation
C([NH:4][NH:5][C:6]([N:8]1[N:12]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[S:10][C:9]1([CH2:27][O:28][CH2:29][O:30][CH3:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])(=O)C.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)Cl.Cl[CH:47](Cl)[CH3:48]>>[F:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[C:11]1[S:10][C:9]([CH2:27][O:28][CH2:29][O:30][CH3:31])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]([C:6]2[O:7][C:47]([CH3:48])=[N:4][N:5]=2)[N:12]=1Participants
Procedure
To a mixture of N′-acetyl-5-(2,5-difluorophenyl)-2-((methoxymethoxy)methyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbohydrazide (0.221 g, 0.491 mmol) and DIEA (0.634 g, 4.91 mmol) in dichloroethane (10 mL) was added POCl3 (0.376 g, 2.45 mmol). After stirring for 30 minutes, the mixture was partitioned between dichloromethane (10 mL) and saturated NaHCO3 (5 mL). The organic layer was extracted with dichloromethane (10 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and chromatographed (20:1 to 10:1 hexanes/ethyl acetate) to provide the final product (0.080 g, 38%). MS ESI (+) m/z 433 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.68 (m, 1H), 7.54 (d, 2H, J=7 Hz), 7.35 (m, 3H), 7.10 (m, 2H), 4.90 (d, 1H, J=11 Hz), 4.74 (m, 2H), 4.52 (d, 1H, J=11 Hz), 3.37 (s, 3H), 2.44 (s, 3H).
Workup
- customthe mixture was partitioned between dichloromethane (10 mL) and saturated NaHCO3 (5 mL)
- extractionThe organic layer was extracted with dichloromethane (10 mL)
- washThe combined organic layers were washed with brine (10 mL)
- dry with materialdried over Na2SO4
- customchromatographed (20:1 to 10:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-c8384146903f47c1899a6b945ffcebb7
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580828B2
Reaction notes
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