Hydrochloric Acid → 36822-06-7

HRID 1605696Notes

Reaction equation

HRID 1605696 reaction equation
CN(C)C=O.[CH2:6]([N:8]([CH2:22][CH3:23])[C:9]1[C:10]2S[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[C:11]=2[N:12]=[CH:13][N:14]=1)[CH3:7].O.[ClH:25]>[Ni].C(OCC)C>[ClH:25].[CH2:22]([N:8]([CH2:6][CH3:7])[C:9]1[CH:10]=[C:11]([C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:16]=2)[N:12]=[CH:13][N:14]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 21547363HCID 21547363, compound

Product 1

HCID 1594552536822-06-7

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.5 ml. of dimethylformamide containing 4-diethylaminobenzothieno[3,2-d]pyrimidine (2.0 g.) is added a large excess of Raney nickel and the resulting mixture heated to reflux. Water is allowed to distill from the reaction mixture until the temperature reaches 150° C. where refluxing is continued with rapid stirring for 48 hours. The solids are filtered and the filtrate concentrated in vacuo to an oil. The residual oil is partitioned between water and chloroform and the organic layer separated and dried over sodium sulfate. Removal of the solvent under reduced pressure provides an oil which when dissolved in ethyl ether and treated with gaseous hydrogen chloride provides 1.4 g. of the hydrochloride salt of the desired product, which is identical in every respect to that synthesized via Method A.

Workup

  1. temperaturethe resulting mixture heated to reflux
  2. distillationto distill from the reaction mixture until the temperature
  3. customreaches 150° C.
  4. temperaturerefluxing
  5. filtrationThe solids are filtered
  6. concentrationthe filtrate concentrated in vacuo to an oil
  7. customThe residual oil is partitioned between water and chloroform
  8. customthe organic layer separated
  9. dry with materialdried over sodium sulfate
  10. customRemoval of the solvent under reduced pressure
  11. customprovides an oil which when
  12. customprovides 1.4 g

Sources & evidence

ORD record
ord-db91820288a6434ca54b4687a46852da
Source dataset
uspto-grants-1976_04
Patent number
US03950525

Reaction notes

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