Hydrochloric Acid → HCID 178507161, compound

HRID 1891040Notes

Reaction equation

HRID 1891040 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([C:10]#[N:11])=[CH:8][N:7]=[C:6]([Cl:12])[N:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[N:21]=[C:22]=[O:23].Cl>C(OCC)(=O)C.CN(C)C=O>[Cl:12][C:6]1[N:5]=[C:4]2[NH:3][C:22](=[O:23])[N:21]([C:15]3[C:14]([Cl:13])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:20])[C:10](=[NH:11])[C:9]2=[CH:8][N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 28011664-Amino-2-chloropyrimidine-5-carbonitrile

Product 1

HCID 178507161HCID 178507161, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.12 g of sodium hydride was added to an N,N-dimethylformamide (35 mL) solution containing 3.0 g of 4-amino-2-chloropyrimidin-5-carbonitrile, and the mixture was stirred for 5 minutes at room temperature. Then, 4.38 g of 2,6-dichlorophenyl isocyanate was added to the reaction mixture, which was then stirred for 1 hour at room temperature. Thereafter, ethyl acetate and a 1 N hydrochloric acid aqueous solution were added to the reaction mixture to separate the organic layer. After washing with saturated saline, the solution was dried with anhydrous magnesium sulfate, and the solvent was distilled away. The deposited solid was solidified using a methanol-ethyl acetate mixed solvent. After leaching, 3.8 g of a white solid was obtained as a subject compound.

Workup

  1. stirringwas then stirred for 1 hour at room temperature
  2. customto separate the organic layer
  3. washAfter washing with saturated saline
  4. dry with materialthe solution was dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-44fb22245fd14b39af6af0a33b3ed4f7
Source dataset
uspto-grants-2013_08
Patent number
US08507505B2

Reaction notes

Loading…