Ammonium thiocyanate → HCID 86746173, compound

HRID 465686Notes

Reaction equation

HRID 465686 reaction equation
[O:1]1[CH:8]2[CH:2]1[CH:3]1[CH2:9][C:7]2([CH2:10][CH3:11])[CH:6]2[CH:4]1O2.[S-:12]C#N.[NH4+]>O1CCCC1>[S:12]1[CH:6]2[CH:4]1[CH:3]1[CH2:9][C:7]2([CH2:10][CH3:11])[CH:8]2[CH:2]1[O:1]2

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 86746174HCID 86746174, compound

Product 1

HCID 86746173HCID 86746173, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6-Epoxyethyl-3-oxatricyclo [3.2.1.0 2.4 ] octane (42g, 0.28mol), ammonium thiocyanate (23g, 0.30 mol) and tetrahydrofuran (125 ml) were placed in a 200-ml egg-plant type flask, and stirred with a magnetic stirrer in a water bath of 50° C. Although first the reaction solution was completely uniform, a white precipitate was deposited about 30 minutes later. 5 hours later, the reaction mixture was suction filtered by a Nutsche to remove the white precipitate, and the filtrate was concentrated by a rotary evaporator. Toluene (250 ml) and water (80 ml) were added to the concentrate, and after separation of the water layer the toluene layer was washed (80 ml ×2). The toluene layer was dried over magnesium sulfate and the toluene was then distilled away by a rotary evaporator. The concentrate was simply distillated under reduced pressure to obtain 6-epithioethyl-3-oxatricyclo [3.2.1,02.4 ] octane (40g, yield 87%). Colorless oil; b.p. 90-93° C./2mmHg; nD 1.5294; IR (neat) 3030(m), 2968(s), 1446(m), 1375(m), 1319(m), 1035(m), 1007(m), 849(s) cm-1 ; 13C NMR(CDCl3) δ23.1, 23.3, 24.1, 24.3, 24.5, 25.3, 26.5, 26.9, 29.7, 30.2, 31.9, 32.3 (CH2); 35.6, 36.2, 36.5, 36.7, 36.9, 37.4, 38.2, 39.0, 41.1, 41.2, 42.1, 42.3, 44.1, 45.3, 47.2, 47.7, 48.5, 48.6, 50.2, 50.4, 50.6, 50.7, 51.0(CH).

Workup

  1. custom5 hours
  2. filtrationfiltered by a Nutsche
  3. customto remove the white precipitate
  4. concentrationthe filtrate was concentrated by a rotary evaporator
  5. additionToluene (250 ml) and water (80 ml) were added to the concentrate
  6. customafter separation of the water layer the toluene layer
  7. washwas washed (80 ml ×2)
  8. dry with materialThe toluene layer was dried over magnesium sulfate
  9. distillationthe toluene was then distilled away by a rotary evaporator

Sources & evidence

ORD record
ord-c4e1c256d43d4662abc7662ed39683da
Source dataset
uspto-grants-1992_10
Patent number
US05153331

Reaction notes

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