Diisopropylethylamine → HCID 86762366, compound

HRID 2367929Notes

Reaction equation

HRID 2367929 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:17]2[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.CCN(C(C)C)C(C)C.Cl[C:37](Cl)([O:39]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)(Cl)Cl>[N:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:17]2[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=[C:37]=[O:39]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 66816065HCID 66816065, compound

Product 1

HCID 86762366HCID 86762366, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Methyl 6-(3-(6-aminohexyloxy)phenyl)picolinate dihydrochloride (19) (40 mg, 0.10 mmol) and DIEA (34 μL, 26 mg, 0.20 mmol) were dissolved in CHCl3 (0.7 mL). Triphosgene (14 mg, 0.047 mmol) was dissolved in CHCl3 (0.3 mL). The solutions were combined and a second portion of DIEA (34 μL, 26 mg, 0.20 mmol) was immediately added. The mixture was left to stand 30 min at RT and evaporated. The residue was dissolved in ethyl acetate and the precipitated DIEA hydrochloride was filtered off. The solvent was evaporated and the crude isocyanate (20) was used directly for the next step.

Workup

  1. waitThe mixture was left
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationthe precipitated DIEA hydrochloride was filtered off
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-02e07cb4799247c1ab9c4d2aaa07f5c9
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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