Diisopropylethylamine → HCID 42643938, compound

HRID 390700

Reaction equation

HRID 390700 reaction equation
[I-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][S:11]/[C:10]/2=[N:14]\[C:15]([N:17]2[CH:21]=[CH:20][N+](C)=[CH:18]2)=[O:16])=[CH:5][CH:4]=1.[CH3:23]NCC#C.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][CH2:12][S:11]/[C:10]/2=[N:14]\[C:15](=[O:16])[N:17]([CH3:18])[CH2:21][C:20]#[CH:23])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96160N-methylpropyn-2-ylamineHCID 87447829(NZ)-N-[3-(4-chlorophenyl)-1,3-thiazolidin-2-ylidene]-3-methylimidazol-3-ium-1-carboxamide iodide

Product 1

HCID 42643938HCID 42643938, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-({[(2Z)-3-(4-Chlorophenyl)-1,3-thiazolidin-2-ylidene]amino}carbonyl)-3-methyl-1H-imidazol-3-ium iodide (97 mg, 0.216 mmol, Example 25B), N-methylprop-2-yn-1-amine (0.020 mL, 0.238 mmol) and diisopropylethylamine (0.041 mL, 0.238 mmol) were heated in acetonitrile at 65° C. After 1 hour, the mixture was concentrated and the residue was purified by chromatography over silica using dichloromethane:methanol 95:5 as eluant to provide the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by chromatography over silica

Sources & evidence

ORD record
ord-325e247ac551463e92ddbca9162e69c5
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Linked notes

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