Triethylamine → HCID 19899254, compound

HRID 1494434Notes

Reaction equation

HRID 1494434 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[CH:15]=[C:14]([N:16]([CH:23]=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[C:12]([CH2:25][CH3:26])[C:11]=1[NH:27][C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=S)[CH3:9].[I-].ClC1C=CC=C[N+]=1C>C(#N)C>[CH2:8]([C:10]1[CH:15]=[C:14]([N:16]([CH:23]=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[C:12]([CH2:25][CH3:26])[C:11]=1[N:27]=[C:28]=[N:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19899242HCID 19899242, compound

Product 1

HCID 19899254HCID 19899254, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

With stirring, 3.2 g of triethylamine are added dropwise at room temperature to 6.0 g of N-[2,6-diethyl-4-(N-formylanilino)phenyl]-N'-tert-butylthiourea and 4.8 g of 2-chloro-1-methylpyridinium iodide in 30 ml of acetonitrile. The reaction mixture is stirred for 1 hour at 70° C. and then concentrated by evaporation at 50° C. on a rotary evaporator. The residue is taken up in 50 ml of hexane and 30 ml of cold water. The hexane phase is separated, washed with water, dried over sodium sulfate and concentrated by evaporation, to give the title compound of formula ##STR21## as a yellowish oil with refractive index nD25 : 1.5840.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at 70° C.
  2. concentrationconcentrated by evaporation at 50° C. on a rotary evaporator
  3. customThe hexane phase is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-976ae3500c7c415a88b8f7f3b9f6b1cc
Source dataset
uspto-grants-1991_06
Patent number
US05026730

Reaction notes

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