Hydrochloric Acid → HCID 44621524, compound

HRID 1809965Notes

Reaction equation

HRID 1809965 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[C:15]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21])#[CH:16].CNCCNC.CCN(CC)CC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].Cl>[Cu]I.C(OCC)(=O)C.CS(C)=O.O>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])[N:13]=[N:12]2)=[CH:3][CH:4]=1)([CH3:10])[CH3:9]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 33557Sodium AzideHCID 87073p-IodocumeneHCID 158970473-Ethynylbenzoic acidHCID 23667548Sodium Ascorbate

Product 1

HCID 44621524HCID 44621524, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

A mixture of 1-iodo-4-isopropylbenzene (5-1) (123 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), 3-ethynylbenzoic acid (5-2) (73 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 μL), Et3N (51 mg, 0.5 mmol), sodium ascorbate (10 mg), DMSO-H2O (v/v 5:1, 1.5 mL) is stirred at room temperature for 2 hours followed by the addition of 2 mL of 1M HCl. The resulting mixture is poured into ethyl acetate (100 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on silica gel (0-100% ethyl acetate in hexane) to give 3-[1-(4-isopropylphenyl)-1H-1,2,3-triazol-4-yl]benzoic acid (5-3) as a white solid. 1H NMR (DMSO-d6) δ (ppm) 9.42 (s, 1H), 8.53 (dd, J=1.6, 1.6 Hz, 1H), 8.20 (ddd, J=8.0, 1.6, 1.2 Hz, 1H), 7.95 (ddd, J=8.0, 1.6, 1.2 Hz, 1H), 7.89 (dm, J=8.8 Hz, 2H), 7.64 (dd, J=8.4, 8.0 Hz, 1H), 7.51 (dm, J=8.8 Hz, 2H), 3.00 (septet, J=6.8 Hz, 1H), 1.26 (d, J=6.8 Hz, 6H). HPLC-MS calculated for C18H17N3O2 (M+H+) 308.13. found 308.10.

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified on silica gel (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-273c4489d0e8416d9f8b28e383b5e68d
Source dataset
uspto-grants-2013_01
Patent number
US08362050B2

Reaction notes

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