Hydrochloric Acid → HCID 66937236, compound

HRID 538214Notes

Reaction equation

HRID 538214 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[N:11]#[C:12][NH2:13].O1CCOCC1.[ClH:20]>CCOCC>[ClH:20].[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12](=[NH:11])[NH2:13])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 312751,4-Dioxane2×HCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 66937236HCID 66937236, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1H-pyrazole-4-carboxylic acid ethyl ester (5.00 g, 35.7 mmol), cyanamide (1.50 g, 35.7 mmol), and dioxane (25 mL) was added a solution of 4M HCl in dioxane (9.80 mL, 39.3 mmol). The reaction mixture was heated to 100° C. for 3 h. The reaction was cooled to 23° C. and Et2O (20 mL) was added. The resulting white precipitate was filtered to yield the titled compound (7.26 g, 93%). 1H NMR (400 MHz, DMSO-d6): 9.65 (br m, 4H), 9.29 (s, 1H), 8.43 (s, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to 23° C.
  2. filtrationThe resulting white precipitate was filtered

Sources & evidence

ORD record
ord-d812840e74e9468d9a5ad7b7b443da63
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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