Dimethylcarbamoyl Chloride → HCID 86679690, compound

HRID 1507082Notes

Reaction equation

HRID 1507082 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:9][N:10]([CH3:14])[C:11](Cl)=[O:12]>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:11](=[O:12])[N:10]([CH3:14])[CH3:9])[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 86679690HCID 86679690, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

3-Amino-5-bromo pyridine (XX) (1.0 g, 5.78 mmol) was dissolved in pyridine and cooled to 0° C. before adding dimethyl carbamyl chloride (XXI) (0.683 g, 6.35 mmol). The reaction mixture was stirred at room temperature for 2 h and then heated overnight at 60° C. under argon. The solution was cooled to room temperature, poured into ice water and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated to a residue to afford 3-(5-bromopyridin-3-yl)-1,1-dimethylurea (XXII) as a brown solid, (1.24 g, 5.09 mmol, 88% yield). 1H NMR (DMSO-d6) δ ppm 8.67-8.64 (m, 2H), 8.23 (d, J=7.8 Hz, 1H), 2.93 (s, 6H); ESIMS found for C8H10BrN3O m/z 245.05 (M+H).

Workup

  1. temperatureheated overnight at 60° C. under argon
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-8b416475537441b4acf92e0ffa9951e3
Source dataset
uspto-grants-2015_12
Patent number
US09221793B2

Reaction notes

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