Water → HCID 12857657, compound

HRID 1395526Notes

Reaction equation

HRID 1395526 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[N:5]=1.[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15].O>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:17])[C:14]([NH:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[N:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 215072-Amino-4,6-dimethylpyridineHCID 24758Sodium hydride

Product 1

HCID 12857657HCID 12857657, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 57% sodium hydride in mineral oil (38.0 gm, 0.90 mole) in dry toluene (600 ml) at 75° under nitrogen atmosphere is added in small portions 2-amino-4,6-dimethylpyridine (52.5 gm, 0.43 mole). The reaction is heated to 100° for one hour and then cooled to 90°. A solution of dimethyl carbamoyl chloride (47.0 g, 0.43 m) in toluene (150 ml) is added dropwise over a one and one-half hour period. Stir for two hours and then cool to ambient temperature. Water (150 ml) is added, the organic layer separated, dried over anhydrous sodium sulfate filtered through charcoal and evaporated. The residue is triturated with cyclohexane (50 ml) and filtered to give analytically pure product (74.0 g., 85% yield), m.p. 105°-108° C.

Workup

  1. temperatureThe reaction is heated to 100° for one hour
  2. temperaturecooled to 90°
  3. customthe organic layer separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered through charcoal
  6. customevaporated
  7. customThe residue is triturated with cyclohexane (50 ml)
  8. filtrationfiltered
  9. customto give analytically pure product (74.0 g., 85% yield), m.p. 105°-108° C.

Sources & evidence

ORD record
ord-e6a1ba7785e349a696261912486fe4b8
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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