Propargyl alcohol → HCID 22101787, compound

HRID 1458241Notes

Reaction equation

HRID 1458241 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[C:10](F)[N:9]=1>C(OC)(C)(C)C>[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[C:10]([O:6][CH2:3][C:4]#[CH:5])[N:9]=1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 22101782HCID 22101782, compound

Product 1

HCID 22101787HCID 22101787, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

3.9 g (0.153 mol) of sodium hydride were introduced, under nitrogen, into 250 ml of methyl tert-butyl ether, with stirring, and 20 ml of propargyl alcohol were then added dropwise with stirring at 25°-30° C. over 20 minutes. After the mixture had been stirred for 30 minutes at 25° C., 32.9 g (0.153 mol) of 2-amino-3-chloro-6-fluoro-5-trifluoromethylpyridine in 100 ml of methyl tert-butyl ether were added in the course of 10 minutes and the mixture was stirred for 14 hours at 25° C. The reaction mixture was extracted with water, dried and concentrated, giving 37.8 g (99% of theory) of the title compound as a colorless oil of ηD24 =1.5217 (Table I, No. 1.035).

Workup

  1. stirringwith stirring at 25°-30° C. over 20 minutes
  2. stirringAfter the mixture had been stirred for 30 minutes at 25° C.
  3. stirringthe mixture was stirred for 14 hours at 25° C
  4. extractionThe reaction mixture was extracted with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c46bd47f218749c28a24c68f2e1e1f96
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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