Acetic Acid → HCID 13849382, compound

HRID 2309363Notes

Reaction equation

HRID 2309363 reaction equation
C(O)C.C(O)(=O)C.[CH3:8][C:9]1[S:32][C:12]2[N:13]=[C:14]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[C:11]=2[CH:10]=1>[Fe].O>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]1[C:11]2[CH:10]=[C:9]([CH3:8])[S:32][C:12]=2[N:13]=[C:14]([N:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]2)[N:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702Ethanol2×HCID 13557207HCID 13557207, compound

Product 1

HCID 13849382HCID 13849382, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

Into a mixed solvent of 8 ml of ethanol, 3.5 ml of water and 4 ml of acetic acid, 1.25 g of 6-methyl-4-(2-nitrophenyl)-2-piperazinyl-thieno[2,3-d]pyrimidine is dissolved, and 1.5 g of iron powder is gradually added at 90° C. over one hour. After the reaction at 90° C. further for 20 minutes, 25 ml of ethanol and 6 ml of water are added. The reaction mixture is filtered by a Celite layer. The Celite layer is washed with hot ethanol and the washings and the filtrate are combined and distilled off under reduced pressure. The residue is treated with 20 ml of 10% aqueous solution of sodium carbonate and with 80 ml of chloroform and filtered by a Celite layer. The chloroform layer is separated and dried over anhydrous sodium sulfate. Chloroform is removed to concentrate and crystallization from chloroform/cyclohexane gives the desired product (0.93 g) which has a melting point of 232°-236° C.

Workup

  1. customAfter the reaction at 90° C. further for 20 minutes
  2. filtrationThe reaction mixture is filtered by a Celite layer
  3. washThe Celite layer is washed with hot ethanol
  4. distillationdistilled off under reduced pressure
  5. additionThe residue is treated with 20 ml of 10% aqueous solution of sodium carbonate and with 80 ml of chloroform
  6. filtrationfiltered by a Celite layer
  7. customThe chloroform layer is separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. customChloroform is removed
  10. concentrationto concentrate
  11. customcrystallization from chloroform/cyclohexane

Sources & evidence

ORD record
ord-46761602a9c94f5ebe76816a4893c0b9
Source dataset
uspto-grants-1987_09
Patent number
US04695568

Reaction notes

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