Sulfuric Acid → HCID 13504796, compound
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[N:16]2[CH2:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:10]2/[CH:11]([N:16]3[CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:13][CH2:14][CH2:15]/2)=[CH:7][CH:8]=1Participants
Procedure
A 0.4 g (1.3 mmole) portion of 1-[2-[[4-(trifluoromethyl)phenyl](hydroxy)methyl]cyclohexyl]azetidine, from step A above was added during 5 min to 4 ml of ice cooled sulfuric acid. The mixture was stirred in ice for 20 min. The resulting mixture was poured into ice, basified with sodium hydroxide, and extracted with six 30 ml portions of chloroform. The chloroform extracts were combined and dried with magnesium sulfate and evaporated to give 0.173 g of (±)-(E)-1-[2-[[4-(trifluoromethyl)phenyl]methylene]cyclohexyl]azetidine. The crystalline p-toluenesulfonic acid salt of this azetidine derivative was prepared, mp 135°-136° C. UV λmax(ε)219 sh (17,350) 222 (17,400) 227 sh (15,250) 246 (11,750) IR,NH Rf 3000b, 2600, 1660 C=C, 1615, 1575, 1495, 1325 SO3 /CF3, 1230, 1215, 1175, 1125, 1065, 1035, 1010, 814 aromatic, 805, 680. NMR (d6DMSO)δ7.75, 7.1 (2d, 4H, aromatic of TSA), 7.6-7.4 (m, 4H, aromatic), 4.1-3.8 (m, 5H, --CH--N(CH2)--CH2 move upfield with addition of NaOH, 2.6-211 (m, 4H, CH2 --C=C+C+CH2 -- of azetidine), 2.3 (s, 3H, CH3), 1.9-1.45 (m,6H, CH2 's).
Workup
- additionThe resulting mixture was poured into ice
- extractionextracted with six 30 ml portions of chloroform
- dry with materialdried with magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-412c3e5ebfc9413e8c06d1dfd386f1e0
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652559
Reaction notes
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