Dimethyl Sulfate → HCID 23023990, compound

HRID 1373857Notes

Reaction equation

HRID 1373857 reaction equation
Br.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)[S:14][CH:15]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:28](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C)C=O>[CH3:28][N:16]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)[C:13]1[S:14][CH:15]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)[N:12]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 23023958HCID 23023958, compound

Product 1

HCID 23023990HCID 23023990, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen stream, N,N-dimethylformamide (1.05 L, 7.0 v/w) was added to ethyl 4-((4-(4-nitrophenyl)-2-thiazolyl)amino)benzoate hydrobromide (150 g, 0.333 mol) obtained in Example 3(1). With stirring under ice-cooling, potassium carbonate (138 g, 0.999 mol) was added carefully. After stirring at room temperature for 20 min., dimethyl sulfate (63.2 ml, 0.666 mol) was added. After stirring at 60° C. for 2 hr., distilled water (1.05 L, 7.0 v/w) was added with stirring under ice-cooling. After stirring under ice-cooling for 1 hr., the resulting crystal were collected by filtration, washed with distilled water (450 mL) and dried in vacuo to give the title compound (127 g, yield 99.3%) as an orange crystal.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 20 min.
  3. stirringAfter stirring at 60° C. for 2 hr
  4. distillation, distilled water (1.05 L, 7.0 v/w)
  5. additionwas added
  6. stirringwith stirring under ice-
  7. temperaturecooling
  8. stirringAfter stirring under ice-
  9. temperaturecooling for 1 hr
  10. filtration, the resulting crystal were collected by filtration
  11. washwashed with distilled water (450 mL)
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c47cf2926e4d40458a40d6b576aa487e
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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