Bromine → HCID 57566634, compound

HRID 217148Notes

Reaction equation

HRID 217148 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:4].[Br:20]Br>C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:20][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:19])([CH3:18])[CH3:1])=[C:7]([C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:17]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 57566646HCID 57566646, compound

Product 1

HCID 57566634HCID 57566634, compoundYield 113%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 24477Sodium ThiosulfateSolvent

Procedure

To a room temperature suspension of 2,2-dimethyl-N-(2-pyrimidin-2-yl-phenyl)-propionamide (˜117 grams, 437 mmoles) in acetic acid (1 L) was added bromine (67 mL, 1.31 moles) as a solution in 100 mL of acetic acid over a 1 hour period. The heterogenous mixture was stirred at room temperature for 5 hours over which time a thick precipitate formed. The mixture was then poured over ice, diluted with 1N Na2S2O3 (2 L), and stirred for 1 hour. The solids were filtered, resuspended in water (2 L), stirred for 1 hour, then filtered and washed with water again. The resulting solids were pumped to dryness at 50° C., resuspended in HOAc (1 L), and treated with bromine (22 mL, 430 mmoles) in acetic acid solution (20 mL) over a 20 minute period. The resulting heterogenous mixture was stirred for 5 hours, then quenched and treated as described above. The resulting solids were vacuum dried at 50° C. to afford the title compound (165 grams) as a tan powder.

Workup

  1. customformed
  2. additionThe mixture was then poured over ice
  3. stirringstirred for 1 hour
  4. filtrationThe solids were filtered
  5. stirringstirred for 1 hour
  6. filtrationfiltered
  7. washwashed with water again
  8. customwere pumped to dryness at 50° C.
  9. stirringThe resulting heterogenous mixture was stirred for 5 hours
  10. customquenched
  11. additiontreated
  12. customdried at 50° C.

Sources & evidence

ORD record
ord-a8f1ace457454eb597ee916ecef6d21d
Source dataset
uspto-grants-2012_06
Patent number
US08193352B2

Reaction notes

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