Ethanol → HCID 13478351, compound

HRID 371470Notes

Reaction equation

HRID 371470 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([NH2:25])=[N:17][C:18]([NH2:24])=[N:19][C:20]=3[CH2:21][CH2:22][CH3:23])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#N.S(=O)(=O)(O)[OH:27].[CH2:31]([OH:33])[CH3:32]>>[NH2:24][C:18]1[N:17]=[C:16]([NH2:25])[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]([O:33][CH2:31][CH3:32])=[O:27])=[CH:4][CH:5]=3)[CH2:14][CH2:13]2)=[C:20]([CH2:21][CH2:22][CH3:23])[N:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13478349HCID 13478349, compound

Product 1

HCID 13478351HCID 13478351, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 1.0 g (2.96 mmole) of 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-propyl-2,4-pyrimidinediamine, 15 ml of 95% ethanol and 15 ml of sulfuric acid was heated under reflux at 100° C. for four hours and cooled. The solution was poured into 200 ml of ice water and filtered. The filtrate was kept cool and neutralized with 50% aqueous sodium hydroxide solution to pH 7. The solid was collected and washed with 50 ml of water. Recrystallization from N,N-dimethylformamide and drying in vacuo at 78° C. for 16 hours gave 0.7 g of the product as a white solid, mp 215°-216° C.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationfiltered
  4. temperatureThe filtrate was kept cool
  5. customThe solid was collected
  6. washwashed with 50 ml of water
  7. customRecrystallization from N,N-dimethylformamide
  8. customdrying in vacuo at 78° C. for 16 hours

Sources & evidence

ORD record
ord-24b676e8d0c14b01abd888ced16dd021
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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