Carbon Disulfide → HCID 20513976, compound

HRID 444508Notes

Reaction equation

HRID 444508 reaction equation
[C:1](=[S:3])=S.[NH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1.C(N(CC)CC)C>CC(C)=O>[N:4]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][N:16]([CH3:17])[CH3:18])[CH:12]=[CH:13][CH:14]=1)=[C:1]=[S:3]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine

Product 1

HCID 20513976HCID 20513976, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of carbon disulphide (8.36 g) in acetone (16 ml) was added dropwise to a stirred solution of 3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (20.8 g) in acetone (60 ml) at -10° to 0° during 15 minutes. A solution of mercuric chloride (27.2 g) in acetone (40 ml) was added slowly at -15° and after the addition the suspension was warmed to 0° and triethylamine (23 g) added dropwise. The suspension was refluxed for 45 minutes then filtered and evaporated to give an oil which was chromatographed (alumina,grade 3/ether). The appropriate eluate was evaporated to a yellow oil consisting of the title compound (8.7 g).

Workup

  1. additionafter the addition the suspension
  2. temperaturewas warmed to 0°
  3. temperatureThe suspension was refluxed for 45 minutes
  4. filtrationthen filtered
  5. customevaporated
  6. customto give an oil which
  7. customwas chromatographed (alumina,grade 3/ether)
  8. customThe appropriate eluate was evaporated to a yellow oil

Sources & evidence

ORD record
ord-e31cb8fb402d421aa78f79d330bbbded
Source dataset
uspto-grants-1981_04
Patent number
US04264614

Reaction notes

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