N-Methylaniline → HCID 10315630, compound

HRID 1198112Notes

Reaction equation

HRID 1198112 reaction equation
Cl[C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[CH3:12][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[N:3]=[C:4]([N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 10315630HCID 10315630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Dichlorothieno[3,2-d]pyrimidine (1 g, 0.0048 mol) and N-methylaniline (5 ml) were heated at 130° for 1 hour. The reaction mixture was diluted with dichloromethane (200 ml) and extracted with 2N hydrochloric acid (3×150 ml). The organic phase was then washed with sodium carbonate, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a brown solid. Recrystallization from methanol gave the title compound, (1.08 g), m.p. 120°-122°.

Workup

  1. extractionextracted with 2N hydrochloric acid (3×150 ml)
  2. washThe organic phase was then washed with sodium carbonate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a brown solid
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-46be276f58dc47e5bc06071cd21a051f
Source dataset
uspto-grants-1994_01
Patent number
US05280026

Reaction notes

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