4,5-Dihydro-2-thiazolamine → 4-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-thiopyran-4-ol

HRID 65662

Reaction equation

HRID 65662 reaction equation
[C:1]1([CH:7]=[C:8]2[C:13](=[O:14])[C:12](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][S:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][C:23]1[S:24][CH2:25][CH2:26][N:27]=1>CC(C)=O>[S:24]1[CH2:25][CH2:26][N:27]=[C:23]1[NH:22][C:13]1([OH:14])[C:8](=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][S:10][CH2:11][C:12]1=[CH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamine2×HCID 336779tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-one

Product 1

HCID 543093604-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-thiopyran-4-olYield 92.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A slurry of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one (5.5 g, 18.9 mmole) in 200 ml of acetone is treated with a solution of 2-amino-2-thiazoline (2.0 g, 19.6 mmole, filtered) in 100 ml of acetone at room temperature. The mixture never becomes homogeneous, but the nature of the solids change (yellow to white). After stirring at room temperature for 2 days, the starting ketone remains as evidenced by tlc. Additional 2-amino-2-thiazoline (1 g, 9.8 mmole, filtered) in 50 ml of acetone is added and the mixture is heated at reflux temperature for 1 day. Upon cooling to room temperature, filtration and washing with acetone affords a combined yield of 6.9 g (92.5%) of product in two crops, m.p. 171°-172.5°).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature for 1 day
  3. temperatureUpon cooling to room temperature
  4. filtrationfiltration
  5. washwashing with acetone

Sources & evidence

ORD record
ord-aaf3d8cc1bea45509c5acd085d8e0556
Source dataset
uspto-grants-1978_12
Patent number
US04128647

Linked notes

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