Diisopropylethylamine → HCID 86762367, compound

HRID 2367932Notes

Reaction equation

HRID 2367932 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:14]2[S:15][CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:18]=2)[CH:11]=[CH:12][CH:13]=1.[Cl:23][C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C>C(OCC)(=O)C>[Cl:23][C:24]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:14]2[S:15][CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:18]=2)[CH:11]=[CH:12][CH:13]=1)=[O:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 66816408HCID 66816408, compound

Product 1

HCID 86762367HCID 86762367, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of methyl 2-(3-(5-hydroxypentyloxy)phenyl)thiazole-4-carboxylate (26), (32 mg, 0.10 mmol, 1.0 eq.) in ethyl acetate (1 mL) was added triphosgene (14 mg, 0.047 mmol, 1.4 eq) dissolved in a minimum amount of ethyl acetate, followed immediately by DIEA (26 μL, 20 mg, 0.15 mmol, 1.5 eq). The mixture was stirred at room temperature for 30 min, the precipitated DIEA hydrochloride was filtered off, and the filtrate evaporated to dryness in vacuo. The oily residue of crude compound 27 was used directly for the next step.

Workup

  1. filtrationthe precipitated DIEA hydrochloride was filtered off
  2. customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ce67fb52da594331aa75a5315afc40e9
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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