Carbon Disulfide → 5-Isothiocyanato-3-methoxymethylisoquinoline

HRID 443814Notes

Reaction equation

HRID 443814 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][O:13][CH3:14])[N:6]=[CH:7]2.C(N(CC)CC)C.[C:22](=S)=[S:23].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[N:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][O:13][CH3:14])[N:6]=[CH:7]2)=[C:22]=[S:23]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 128748525-Amino-3-methoxymethylisoquinoline

Product 1

HCID 128748545-Isothiocyanato-3-methoxymethylisoquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

A solution of 5-amino-3-methoxymethylisoquinoline (22.9 g) in pyridine (80 cc) is added dropwise, whilst stirring and at a temperature of about -10° C., to a solution of triethylamine (17 cc) and carbon disulphide (55 cc) in pyridine (80 cc). After 4 hours at -10° C., a solution of dicyclohexylcarbodiimide (25.2 g) in pyridine (80 cc) is added dropwise. Stirring is maintained for 3 hours at a temperature which changes from -10° to 20° C., and then for 20 hours at a temperature of about 20° C. The mixture is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg), the residue is taken up in methylene chloride (800 cc), and insoluble material is removed by filtration and the filtrate is evaporated to dryness at 40° C. under reduced pressure (40 mm Hg). The residue is taken up in diisopropyl ether (1 liter; an insoluble material is removed by filtration and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). 5-Isothiocyanato-3-methoxymethylisoquinoline (18.5 g), m.p. 88° C., is obtained.

Workup

  1. temperatureis maintained for 3 hours at a temperature which
  2. customchanges from -10° to 20° C.
  3. waitfor 20 hours at a temperature of about 20° C
  4. customThe mixture is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg)
  5. custominsoluble material is removed by filtration
  6. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (40 mm Hg)
  7. customan insoluble material is removed by filtration
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)

Sources & evidence

ORD record
ord-9cbb245508844cb2b76b11161402d370
Source dataset
uspto-grants-1981_04
Patent number
US04261992

Reaction notes

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