Ammonium Chloride → HCID 66669477, compound

HRID 2228835Notes

Reaction equation

HRID 2228835 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][OH:14])[CH:2]=1.CC(C)([O-])C.[K+].[C:21]1([N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH4+].[Cl-]>C1COCC1.CC(OC)(C)C>[C:21]1([N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28]([O:14][CH2:13][C:12]#[C:11][C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:29])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 65741N,N-Diphenylcarbamic chlorideHCID 6501423-Quinolin-3-ylprop-2-yn-1-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 66669477HCID 66669477, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a dry three-necked round-bottom flask equipped with nitrogen inlet and overhead stirrer was charged 3-(3-quinolyl)-2-propyn-1-ol (5 g, 27 mmol) in THF (50 ml) and the solution was cooled to 0° C. Potassium t-butoxide (3.6 g, 32 mmol) was then added followed by diphenylcarbamoyl chloride (6.9 g, 29.7 mmol). The mixture was stirred for 2 hours at 0° C. and then allowed to warm up to room temperature over a period of 6 hours by which time the reaction was determined to be complete. The reaction mixture was worked up with MTBE (100 ml) and 10% NH4Cl (50 ml) and was concentrated to ¼ the volume. Heptane (75 ml) was added and the product was crystallised out. Yield=8.3 g (80%).

Workup

  1. customTo a dry three-necked round-bottom flask equipped with nitrogen inlet
  2. temperatureto warm up to room temperature over a period of 6 hours by which time the reaction
  3. concentrationwas concentrated
  4. additionHeptane (75 ml) was added
  5. customthe product was crystallised out

Sources & evidence

ORD record
ord-2b005e77eb3b4f58982663b33d3bc7e6
Source dataset
uspto-grants-2002_07
Patent number
US06417366B2

Reaction notes

Loading…