Imidazole → HCID 86673491, compound

HRID 629000Notes

Reaction equation

HRID 629000 reaction equation
N1([C:6]([N:8]2[CH:12]=[CH:11][N:10]=C2)=[S:7])C=CN=C1.N1C=CN=C1.[CH3:18][O:19][C:20]1[C:21]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[N:24][CH:25]=1.[C:39]1(N)[C:40](N)=CC=[CH:43][CH:44]=1>C(Cl)Cl.CC#N>[NH2:10][C:11]1[CH:43]=[CH:44][CH:39]=[CH:40][C:12]=1[NH:8][C:6]([NH:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[N:22]=[C:21]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:20]([O:19][CH3:18])=[CH:25][N:24]=2)=[CH:27][CH:28]=1)=[S:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 7243O-PhenylenediamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 67295475HCID 67295475, compound

Product 1

HCID 86673491HCID 86673491, compoundYield 70.18%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of di-imidazol-1-yl-methanethione (0.5 g, 1.50 eq.), imidazole (0.03 g, 0.3 eq.) and CH3CN (7 ml) was added dropwise to 4-(5-methoxy-4-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (0.5 g, 1.0 eq.) in CH2Cl2 (5 ml) at 0° C. When S.M. is disappear in TLC, dropping benzene-1,2-diamine (0.37 g, 3.0 eq) to the solution for 3 hrs at 50° C. The solvent was removed in vacuo. The resulting solution was crystallized in a EA solution, and filtered to given a light yellow solid, which was then dried in vacuo to give of a product (0.53 g, 70.18%).

Workup

  1. customfor 3 hrs
  2. customat 50° C
  3. customThe solvent was removed in vacuo
  4. customThe resulting solution was crystallized in a EA solution
  5. filtrationfiltered
  6. customwas then dried in vacuo

Sources & evidence

ORD record
ord-451940b3f4284d4690bebb75492e7d95
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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