Triethylamine → HCID 15603447, compound

HRID 505459Notes

Reaction equation

HRID 505459 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([NH2:27])[CH:20]=3)=[CH:17][N:16]=[N:15]2)[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11].[CH2:28]([N:30](CC)[CH2:31]C)C.ClC(Cl)([O:38][C:39](=O)[O:40]C(Cl)(Cl)Cl)Cl>ClCCl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([N:14]2[C:18]([C:19]3[CH:20]=[CH:21][C:22]([N:30]([CH3:31])[CH3:28])=[CH:23][CH:24]=3)=[CH:17][N:16]=[N:15]2)[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11].[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[N:14]([C:6]3[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=3)[N:15]=[N:16][CH:17]=2)=[CH:20][C:21]=1[NH:27][C:39](=[O:38])[O-:40]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 66678812HCID 66678812, compound

Product 2

HCID 15603447HCID 15603447, compoundHCID 86615575HCID 86615575, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-(3,4,5-trimethoxy-phenyl)-5-(3-amino-4-methoxy-phenyl)-1H-[1,2,3]triazole hydrochloride (300 mg) and triethylamine (0.22 mL, 1.60 mmol) in dichloromethane (3 mL) is added slowly to a solution of triphosgene (77 mg, 0.26 mmol) in dichloromethane (5 mL) at 0° C. under nitrogen atmosphere. The reaction mixture is stirred for 30 min at room temperature, and then cooled to 0° C. before the addition of PEG (1.53 g, 0.76 mmol) and triethylamine (0.12 mL, 0.77 mmol) in 2 ml of dichloromethane. The resulting reaction mixture is stirred for 3 h. and washed with NaHCO3 solution. The aqueous layer is extracted with dichloromethane (2×), and the combined organic layers are washed with saturated NaCl solution, dried over Na2SO4 and evaporated. The crude product is purified by silica gel column chromatography (20% MeOH in EA) to give desired product PEG-2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazol-5-yl)phenylcarbamate.

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred for 3 h.
  3. washwashed with NaHCO3 solution
  4. extractionThe aqueous layer is extracted with dichloromethane (2×)
  5. washthe combined organic layers are washed with saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude product is purified by silica gel column chromatography (20% MeOH in EA)

Sources & evidence

ORD record
ord-e69569bf461c47afb0fff4890d316f99
Source dataset
uspto-grants-2010_08
Patent number
US07781462B2

Reaction notes

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