Triethylamine → HCID 13281427, compound

HRID 1940490Notes

Reaction equation

HRID 1940490 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]#[CH:12])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.C(N(CC)CC)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]([N:6]=[C:22]=[O:24])=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[CH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

Product 1

HCID 13281427HCID 13281427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-chloro-2 fluoro-5-[(2-propynyl)oxy]-aniline (5.0 gm) and triethylamine (5.1 gm) in CH2Cl2 (100 mL) under N2, at 10° C. (ice-bath) was added triphosgene portionwise. The solution was heated to reflux for 5 hours. The solution was evaporated under vacuum and suspended in Et2O (200 mL). The suspension was filtered and the filtrate evaporated to dryness to give the title compound as a white solid (4.68 gm), 83%; IR (nujol, cm-1): 3295 (C≡C) and 2257 (N=C=O). This crude product was used as such in the next reaction.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. customThe solution was evaporated under vacuum
  4. filtrationThe suspension was filtered
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-0f3eb956cb94402bab8579d639dff14f
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

Loading…