Nitrogen → HCID 4913285, compound

HRID 381617Notes

Reaction equation

HRID 381617 reaction equation
N1CCOCC1.[C:7]1([C:13](=O)[CH2:14][C:15](=O)[CH3:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[C:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1)([OH:22])=[O:21].N#N.[N-]=C=O>CO.C(Cl)Cl>[CH3:16][C:15]1[CH:14]=[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:29]([C:26]2[CH:25]=[CH:24][C:23]([C:20]([OH:22])=[O:21])=[CH:28][CH:27]=2)[N:30]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 7166BenzoylacetoneHCID 8083MorpholineHCID 905474-Hydrazinobenzoic acid hydrochlorideHCID 105034Isocyanate2×

Product 1

HCID 4913285HCID 4913285, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of polymer-supported morpholine (Example 12), 1-phenyl-1,3-butanedione (81.5 mg, 0.5 mmol) and 4-carboxyphenyl hydrazine hydrochloride (113 mg, 0.6 mmol) in MeOH (2 mL) was shaken for 2.5 hours. The methanol was blown off under a stream of N2. DCM (4 mL) and polymer-supported isocyanate (Example 4A, 350 mg) were added and the reaction mixture shaken for 16 hours. An additional portion of polymer-supported isocyanate (120 mg) was added. After 4 hours the resin was filtered and washed with DCM (2×1.5 mL). The combined organic phases, when concentrated to dryness, gave 4-(3-methyl-5-phenyl-pyrazol-1-yl)-benzoic acid (67 mg, 48%), mp 159-162° C. Predicted mass for (C17H14N2O2+H)+, 278.1055.

Workup

  1. stirringthe reaction mixture shaken for 16 hours
  2. filtrationAfter 4 hours the resin was filtered
  3. washwashed with DCM (2×1.5 mL)
  4. concentrationThe combined organic phases, when concentrated to dryness

Sources & evidence

ORD record
ord-0a65c91df12f4451bfba0eff80a44bad
Source dataset
uspto-grants-2001_10
Patent number
US06306959B1

Reaction notes

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