Ammonia → HCID 10199053, compound

HRID 345509Notes

Reaction equation

HRID 345509 reaction equation
Cl.[CH3:2][N:3]([CH3:20])[C:4]1[C:8]([CH2:9][C:10](O)=[O:11])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[NH:6][N:5]=1.C([N:23](CC)CC)C.C(=O)=O.CC(C)=O.ClC(OCC)=O.N>C(Cl)Cl>[CH3:2][N:3]([CH3:20])[C:4]1[C:8]([CH2:9][C:10]([NH2:23])=[O:11])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[NH:6][N:5]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18522661Acetone cardiceHCID 67913256HCID 67913256, compound

Product 1

HCID 10199053HCID 10199053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4.5 g (0.015 mole) of 3-(dimethylamino)-5-(4-methylphenyl)pyrazole-4-acetic acid monohydrochloride and 4 ml (0.03 mole) of triethylamine in 75 ml of methylene chloride was stirred under nitrogen until all the solids dissolved, then cooled to -30° C. in a dry ice/acetone batch and treated with 1.7 g (0.0152 mole) of ethyl chloroformate added dropwise through a septum with a syringe and needle. The reaction mixture was cooled to 0° C. with an ice-brine bath and ammonia (5 ml in 10 ml of methylene chloride) was added. The reaction was stirred for 16 hours as it warmed to ambient temperature.

Workup

  1. dissolutiondissolved
  2. additionadded dropwise through a septum with a syringe
  3. stirringThe reaction was stirred for 16 hours as it
  4. temperaturewarmed to ambient temperature

Sources & evidence

ORD record
ord-412acffc379845b6a5f6b7c9e8c95266
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Reaction notes

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