4,5-Dihydro-2-thiazolamine → 2,3,8,9-Tetrahydro-5-(4-methoxy-2,5-dimethylphenyl)-9-[(4-methoxy-2,5-dimethylphenyl)methylene]-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidine

HRID 65677

Reaction equation

HRID 65677 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH:10]=[C:11]2[C:16](=O)[C:15](=[CH:18][C:19]3[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[CH:21][C:20]=3[CH3:28])[CH2:14][O:13][CH2:12]2)=[C:5]([CH3:29])[CH:4]=1.[NH2:30][C:31]1[S:32][CH2:33][CH2:34][N:35]=1>C(Cl)(Cl)Cl.CCO>[CH3:27][O:26][C:22]1[C:23]([CH3:25])=[CH:24][C:19]([CH:18]2[N:35]3[CH2:34][CH2:33][S:32][C:31]3=[N:30][C:16]3[C:11](=[CH:10][C:6]4[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[CH3:29])[CH2:12][O:13][CH2:14][C:15]2=3)=[C:20]([CH3:28])[CH:21]=1

Participants

5

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 53782418Tetrahydro-3,5-bis[(4-methoxy-2,5-dimethylphenyl)methylene]-4H-pyran-4-one

Product 1

HCID 217866822,3,8,9-Tetrahydro-5-(4-methoxy-2,5-dimethylphenyl)-9-[(4-methoxy-2,5-dimethylphenyl)methylene]-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidineYield 46.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A stirred solution of tetrahydro-3,5-bis[(4-methoxy-2,5-dimethylphenyl)methylene]-4H-pyran-4-one (3.0 g, 7.6 mmole) and 2-amino-2-thiazoline (1.0 g, 9.7 mmole) in 75 ml of CHCl3 is heated at reflux temperature for 72 hours. After cooling, the solution is filtered to remove a small amount of insoluble material. The solvent is evaporated to give an oily residue. A solution of this material in 25 ml of EtOH yields 1.7 g of light yellow solid, m.p. 195°-197°. Crystallization from 20 ml of 10% DMF/MeOH gives 1.3 g (35%) of cream colored solid, m.p. 196°-198°.

Workup

  1. temperatureat reflux temperature for 72 hours
  2. temperatureAfter cooling
  3. filtrationthe solution is filtered
  4. customto remove a small amount of insoluble material
  5. customThe solvent is evaporated
  6. customto give an oily residue

Sources & evidence

ORD record
ord-f8d52a0270014774bde0a6d1b66b7a76
Source dataset
uspto-grants-1978_12
Patent number
US04128648

Linked notes

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