Carbon Disulfide → 3-Ethoxymethyl-5-isothiocyanatoisoquinoline

HRID 443808Notes

Reaction equation

HRID 443808 reaction equation
[C:1](=[S:3])=S.C(N(CC)CC)C.[NH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[C:15]([CH2:22][O:23][CH2:24][CH3:25])[N:16]=[CH:17]2.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH2:24]([O:23][CH2:22][C:15]1[N:16]=[CH:17][C:18]2[C:13]([CH:14]=1)=[C:12]([N:11]=[C:1]=[S:3])[CH:21]=[CH:20][CH:19]=2)[CH3:25]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 128748535-Amino-3-ethoxymethylisoquinoline

Product 1

HCID 130143223-Ethoxymethyl-5-isothiocyanatoisoquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution of carbon disulphide (16 cc) and triethylamine (4.5 cc) in pyridine (20 cc) is cooled to -10° C. A solution of 5-amino-3-ethoxymethylisoquinoline (6.5 g) in pyridine (20 cc) is added dropwise in the course of 5 minutes. The mixture is stirred for 3 hours at -10° C. and a solution of dicyclohexylcarbodiimide (6.6 g) in pyridine (20 cc) is then added. Stirring is continued, whilst leaving the reaction mixture to return to a temperature of about 20° C. The mixture is stirred for 24 hours at this temperature and then concentrated to dryness at 50° C. under reduced pressure (20 mm Hg). The residue is taken up in methylene chloride (25 cc). An insoluble material is filtered off and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). The residue is taken up in diisopropyl ether (200 cc). The isoluble yellow solid is isolated by filtration, washed with diisopropyl ether (20 cc) and dried. 3-Ethoxymethyl-5-isothiocyanatoisoquinoline (7 g), melting at 66° C., is obtained.

Workup

  1. stirringStirring
  2. customwhilst leaving the reaction mixture
  3. customto return to a temperature of about 20° C
  4. stirringThe mixture is stirred for 24 hours at this temperature
  5. concentrationconcentrated to dryness at 50° C. under reduced pressure (20 mm Hg)
  6. filtrationAn insoluble material is filtered off
  7. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)
  8. customThe isoluble yellow solid is isolated by filtration
  9. washwashed with diisopropyl ether (20 cc)
  10. customdried

Sources & evidence

ORD record
ord-c96a8a3d31064de68883da0eb44a3cb8
Source dataset
uspto-grants-1981_04
Patent number
US04261993

Reaction notes

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