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

HRID 65661Notes

Reaction equation

HRID 65661 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10](=[CH2:16])[CH:11]=[CH:12][C:13](=O)[CH:14]=2)=[CH:5][CH:4]=1.[NH2:17][C:18]1[S:19][CH2:20][CH2:21][N:22]=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:22]3[CH2:21][CH2:20][S:19][C:18]3=[N:17][C:13]3[C:12](=[CH:9][C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:11][S:10][CH2:16][C:14]2=3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 86736189(4-methoxyphenyl)-methylene-4H-thiopyran-4-one

Product 1

HCID 217866732,3,8,9-Tetrahydro-5-(4-methoxyphenyl)-9-[(4-methoxyphenyl)methylene]-5H,6H-thiazolo[3,2-a]thiopyrano[4,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tetrahydro-3,5-bis[(4-methoxyphenyl)-methylene-4H-thiopyran-4-one (4.9 g, 14 mmole) and 2-amino-2-thiazoline (1.8 g, 17.6 mmole) in acetone (300 ml) is heated at reflux temperature overnight. The precipitate (4.7 g) collected is a mixture of starting ketone and intermediate aminol (4-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis[(4-methoxyphenyl)methylene]thiopyran-4-ol) in a ratio of 4:6.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature overnight
  3. customThe precipitate (4.7 g) collected
  4. additiona mixture of starting ketone and intermediate aminol (4-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis[(4-methoxyphenyl)methylene]thiopyran-4-ol) in a ratio of 4:6

Sources & evidence

ORD record
ord-909f5e2cf2674dd8ac623efeecb90ce4
Source dataset
uspto-grants-1978_12
Patent number
US04128647

Reaction notes

Loading…