N-Methylaniline → HCID 10066220, compound

HRID 1198109Notes

Reaction equation

HRID 1198109 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=1.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:10]=[C:11]([N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:19])[C:12]2[S:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 10423551HCID 10423551, compound

Product 1

HCID 10066220HCID 10066220, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Methylphenylamino)-4-chlorothieno[3,2-d]-pyrimidine (1.5 g, 0.0054 mol) and N-methylaniline (1.16 g, 0.0054 mol) were heated in an oil bath at 140° for 2 hours. The reaction mixture was diluted with dichloromethane (100 ml) and washed with 2N hydrochloric acid (3×100 ml), then sodium carbonate solution. The dichloromethane extracts were dried over magnesium sulphate, filtered and evaporated to give a solid. Recrystallization from methanol gave the title compound, (0.75 g) m.p. 198°-200°.

Workup

  1. washwashed with 2N hydrochloric acid (3×100 ml)
  2. dry with materialThe dichloromethane extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a solid
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-782c6cac6b354fb784036486d31f4a59
Source dataset
uspto-grants-1994_01
Patent number
US05280026

Reaction notes

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