Triethylamine → HCID 178499179, compound

HRID 2066968Notes

Reaction equation

HRID 2066968 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][NH:7][N:6]=1)=[O:4].C(N(CC)CC)C.[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21](Cl)=[O:22]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:21](=[O:22])[C:20]2[C:19]([Cl:18])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:28])=[CH:8][NH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 178499176HCID 178499176, compound

Product 1

HCID 178499179HCID 178499179, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 4-amino-1H-pyrazole-3-carboxylic acid methyl ester (0.634 Kg, 4.49 mol, 1 wt) in 1,4-dioxane (8.90 L, 9 vol) under nitrogen was treated with triethylamine (0.761 L, 5.46 mol, 1.2 vol) followed by 2,6-dichlorobenzoyl chloride (0.710 L, 4.96 mol, 0.72 vol) such that the internal temperature was maintained in the range 20 to 25° C. Residual 2,6-dichlorobenzoyl chloride was washed in with a line rinse of 1,4-dioxane (0.990 L, 1 vol) and the reaction mixture stirred at 18 to 25° C. until complete (16 hours) by TLC analysis (eluent: ethyl acetate:heptanes 3:1; Rf amine 0.25, Rf product 0.65). The reaction mixture was filtered, the filter-cake washed with 1,4-dioxane (2×0.990 L, 2×1 vol) and the combined filtrates (red) progressed to Stage 4 without further isolation.

Workup

  1. washResidual 2,6-dichlorobenzoyl chloride was washed in with a line
  2. washrinse of 1,4-dioxane (0.990 L, 1 vol)
  3. filtrationThe reaction mixture was filtered
  4. washthe filter-cake washed with 1,4-dioxane (2×0.990 L, 2×1 vol)

Sources & evidence

ORD record
ord-019b9c0b866c411ea15a1d80f0bf9cfd
Source dataset
uspto-grants-2012_10
Patent number
US08293767B2

Reaction notes

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