Sulfuric Acid → HCID 13504796, compound

HRID 1719529Notes

Reaction equation

HRID 1719529 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]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13504836HCID 13504836, compound

Product 1

HCID 13504796HCID 13504796, compound

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)219sh(17,350) 222(17,400) 227sh(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

  1. additionThe resulting mixture was poured into ice
  2. extractionextracted with six 30 ml portions of chloroform
  3. dry with materialdried with magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-0adfd3a06200485bb3139acc89740cd7
Source dataset
uspto-grants-1985_09
Patent number
US04540690

Reaction notes

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