Hydrochloric Acid → HCID 178507161, compound

HRID 2088726Notes

Reaction equation

HRID 2088726 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 of 3.0 g of 4-amino-2-chloropyrimidine-5-carbonitrile, and stirred at room temperature for 5 minutes. 4.38 g of 2,6-dichlorophenyl isocyanate was added to the reaction liquid, and stirred at room temperature for 1 hour. Ethyl acetate and aqueous 1 N hydrochloric acid solution were added to the reaction solution, and the organic layer was separated. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The precipitated solid was solidified with a mixed solvent of methanol/ethyl acetate and taken out through filtration to obtain 3.8 g of the entitled compound as a white solid.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. washThis was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away
  6. filtrationtaken out through filtration

Sources & evidence

ORD record
ord-c57ce19a0c2c4ce3b4dbe59ece31189a
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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