Water → HCID 20541623, compound

HRID 2286120Notes

Reaction equation

HRID 2286120 reaction equation
[C:1](Cl)(Cl)=[S:2].O.[C:6]([C:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7].C(N(CC)CC)C>C(Cl)Cl>[N:14]([C:8]1([CH2:6][CH3:7])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[C:1]=[S:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 1216911-Ethynylcyclohexylamine

Product 1

HCID 20541623HCID 20541623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thiophosgene (140 g) was dissolved in 250 ml methylene chloride and 250 ml water was added. To the two-phase system was added dropwise a solution of 1-ethynyl-1-amino-cyclohexane (123 g) and triethylamine (101 g) in 250 ml methylene chloride. The mixture was cooled to prevent refluxing. The mixture was stirred at room temperature for two hours, phase separated, and the organic phase was collected. This layer was dried (MgSO4) and stripped, and the residue was dissolved in diethyl ether, filtered and stripped to yield a dark brown oil. A small portion of the oil was purified on a silica gel column (3×10 cm) with hexane elution to yield 1-isothiocyano-1-ethyl-cyclohexane (A), 5.9 g.

Workup

  1. temperatureThe mixture was cooled
  2. temperatureto prevent refluxing
  3. customphase separated
  4. customthe organic phase was collected
  5. dry with materialThis layer was dried (MgSO4)
  6. dissolutionthe residue was dissolved in diethyl ether
  7. filtrationfiltered
  8. customto yield a dark brown oil
  9. customA small portion of the oil was purified on a silica gel column (3×10 cm) with hexane elution

Sources & evidence

ORD record
ord-d5fe517419c0481fad7896950ecfd7eb
Source dataset
uspto-grants-1982_04
Patent number
US04326876

Reaction notes

Loading…