Diisopropylethylamine → HCID 89783700, compound

HRID 1056363Notes

Reaction equation

HRID 1056363 reaction equation
[NH2:1][C:2]1[C:12]([Br:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:3]2[C:2]=1[NH:1][C:15](=[O:17])[N:6]([CH2:7][CH3:8])[C:4]2=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 82547484HCID 82547484, compound

Product 1

HCID 89783700HCID 89783700, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-amino-3-bromo-N-ethylbenzamide (2.0 g, 8.23 mmol, 481a), triphosgene (0.830 g, 2.80 mmol, Sigma Aldrich,), DCM (28.0 mL), and DIPEA (1.6 mL, 8.95 mmol) was set stirring at 60° C. with a condenser for 4 h. The mixture was concentrated under reduced pressure to a yellow residue. It was adsorbed onto silica and purified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold). The product fractions were combined and concentrated under reduced pressure to give the product as a white solid (736 mg, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.52 (1H, s) 7.95 (1H, dd, J=7.82, 1.37 Hz) 7.98 (1H, dd, J=7.82, 1.37 Hz) 7.15 (1H, t, J=7.82 Hz) 3.93 (2H, q, J=7.04 Hz) 1.15 (3H, t, J=7.04 Hz). m/z (ESI, +ve) 268.9 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure to a yellow residue
  2. custompurified on 24 g SiO2 (eluent: 0-100% EtOAc/hexanes over 25 min, RediSep Gold)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75addc7ca43a4519beec053123b37cc9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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