Dimethylformamide → HCID 23024013, compound

HRID 1373858Notes

Reaction equation

HRID 1373858 reaction equation
CN(C)C=O.[CH3:6][N:7]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1)[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[N:12]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(N(CC)CC)C>O>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]2[N:12]=[C:8]([N:7]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=3)[CH3:6])[S:9][CH:10]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24489Sodium DithioniteHCID 23023990HCID 23023990, compound

Product 1

HCID 23024013HCID 23024013, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen stream, N,N-dimethylformamide (1.20 L, 10.0 v/w) was added to ethyl 4-(N-methyl-N-(4-(4-nitrophenyl)-2-thiazolyl)amino)benzoate (123 g, 0.321 mol) obtained in Example 3(2). With stirring at room temperature, sodium hydrosulfite (80% purity, 210 g, 0.963 mol) was added. After stirring at room temperature for 10 min., distilled water (123 ml, 1.0 v/w) was added carefully. After stirring at 100° C. for 1.5 hr., triethylamine (223 ml, 1.61 mol) was added at 80° C., and the mixture was cooled to room temperature with water. After stirring at room temperature for 1 hr., distilled water (1.1 L, 9.0 v/w) was added. After stirring at room temperature for 30 min., the mixture was extracted twice with ethyl acetate (1.20 L) and the organic layer was washed successively with distilled water (400 ml) and saturated brine (400 ml), and dried over magnesium sulfate (60 g). The magnesium sulfate was filtered off, the solvent was evaporated, the residue was boiled with toluene and dried in vacuo to give the title compound (67.0 g, yield 63.0%) as a yellow to orange solid.

Workup

  1. stirringAfter stirring at room temperature for 10 min.
  2. distillationdistilled water (123 ml, 1.0 v/w)
  3. additionwas added carefully
  4. stirringAfter stirring at 100° C. for 1.5 hr
  5. stirringAfter stirring at room temperature for 1 hr
  6. distillation, distilled water (1.1 L, 9.0 v/w)
  7. additionwas added
  8. stirringAfter stirring at room temperature for 30 min.
  9. extractionthe mixture was extracted twice with ethyl acetate (1.20 L)
  10. washthe organic layer was washed successively with distilled water (400 ml) and saturated brine (400 ml)
  11. dry with materialdried over magnesium sulfate (60 g)
  12. filtrationThe magnesium sulfate was filtered off
  13. customthe solvent was evaporated
  14. customdried in vacuo

Sources & evidence

ORD record
ord-4d5fa0d4c71c4431b1eebb99b36a6eb0
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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