Triethylamine → HCID 18693225, compound

HRID 1870749Notes

Reaction equation

HRID 1870749 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]([CH3:26])=[CH2:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH:19][NH2:20])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].C(N(CC)CC)C.[C:34](Cl)(Cl)=[S:35]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]([CH3:26])=[CH2:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]2[O:18][C:34](=[S:35])[NH:20][N:19]=2)=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 18693261HCID 18693261, compound

Product 1

HCID 18693225HCID 18693225, compoundYield 206.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-[N-(5-Bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carbohydrazide (reference example 26) (750 mg, 1.78 mmol) was dissolved in THF (25 ml) and triethylamine (0.57 ml, 3.91 mmol) added followed by thiophosgene (0.1 ml, 1.96 mmol). The solution was stirred at ambient temperature under argon for 3 hours, then the THF removed in vacuo, water (75 ml) added, and then acetic acid was added dropwise till the mixture was at pH 5. The mixture was extracted with ethyl acetate(3×200 ml) and the combined organic phases washed with water and saturated brine (100 ml of each), dried (MgSO4) and concentrated in vacuo to give the title compound as a gum (1.7 g) which was purified by MPLC (98:2 dichloromethane:methanol), to give a solid foam (230 mg 28%).

Workup

  1. customthe THF removed in vacuo, water (75 ml)
  2. additionadded
  3. additionacetic acid was added dropwise till the mixture
  4. extractionThe mixture was extracted with ethyl acetate(3×200 ml)
  5. washthe combined organic phases washed with water and saturated brine (100 ml of each),
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63b5dd1b6fbe4f40b786367a44cff7b2
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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