Triethylamine → HCID 20093450, compound

HRID 274620Notes

Reaction equation

HRID 274620 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1.C(N(CC)CC)C.[CH3:16][CH2:17][CH2:18][C:19](Cl)=[O:20].OP([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:19]([NH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1)(=[O:20])[CH2:18][CH2:17][CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 24450Potassium Phosphate, DibasicHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 20093450HCID 20093450, compoundYield 114.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution under nitrogen of 5-amino-1,3-dimethylpyrazole (7.09 g, 63.8 mmol) and triethylamine (10 mL) in sieve-dried methylene chloride (100 mL) was chilled in an ice-bath and n-butyryl chloride (7.3 mL, 70.3 mmol) was added dropwise. After 1 hour, the reaction mixture was shaken with 50 mL of 1M K2HPO4 solution and the aqueous phase was further extracted with CH2Cl2 (2×70 mL). The organic phase was dried over MgSO4, filtered and then evaporated to dryness to give 13.2 g of an orange-yellow oil. This was purified by chromatography on SiO2 (300 g), developing with EtOAc/hexane (45:55) to give the Step A compound (10.53 g; 91%) as an oil. 1H NMR (200 MHz, CDCl3), δ 6.00 (s, 1H), 3.65 (s, 3H), 2.37 (t, 2H, J=9 Hz), 2.22 (s, 3H), 1.62-1.90 (m, 2H), 1.01 (t, 3H, J=9 Hz).

Workup

  1. extractionthe aqueous phase was further extracted with CH2Cl2 (2×70 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-804a674fcd2f43219c5f0e1599787e7a
Source dataset
uspto-grants-1995_02
Patent number
US05389660

Reaction notes

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