4-[(4,5-Dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-pyran-4-ol → 2,3,8,9-Tetrahydro-5-phenyl-9-(phenylmethylene)-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidine

HRID 65671Notes

Reaction equation

HRID 65671 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[NH:6][C:7]1(O)[C:12](=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][CH2:9][C:8]1=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:21]1([CH:20]2[N:3]3[CH2:4][CH2:5][S:1][C:2]3=[N:6][C:7]3[C:12](=[CH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:11][O:10][CH2:9][C:8]2=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 541285554-[(4,5-Dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-pyran-4-ol

Product 1

HCID 217866782,3,8,9-Tetrahydro-5-phenyl-9-(phenylmethylene)-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

To a stirred suspension of 4-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-pyran-4-ol (2.5 g, 6.6 mmole) in toluene (100 ml) is added slowly a solution of titanium tetrachloride (0.63 g, 3.3 mmole) in toluene (6.1 ml). The yellow mixture is heated at reflux temperature for 45 minutes.

Workup

  1. temperatureThe yellow mixture is heated
  2. temperatureat reflux temperature for 45 minutes

Sources & evidence

ORD record
ord-fa787d48d6454a8fbf1f87b6653fd744
Source dataset
uspto-grants-1978_12
Patent number
US04128648

Reaction notes

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