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

HRID 65670

Reaction equation

HRID 65670 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.[C:7]1([CH:13]=[C:14]2[C:19](=[O:20])[C:18](=[CH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][O:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)(Cl)Cl>CC(C)=O>[S:3]1[CH2:4][CH2:5][N:6]=[C:2]1[NH:1][C:19]1([OH:20])[C:18](=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][O:16][CH2:15][C:14]1=[CH:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 156894,5-Dihydro-2-thiazolamineHCID 286335tetrahydro-3,5-bis(phenylmethylene)-4H-pyran-4-one

Product 1

HCID 541285554-[(4,5-Dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-pyran-4-olYield 45.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2-amino-2-thiazoline (2.2 g, 22 mmole) in 100 ml of acetone is added to a suspension of tetrahydro-3,5-bis(phenylmethylene)-4H-pyran-4-one (5.0 g, 18 mmole) in 50 ml of acetone and heated at reflux temperature for 5 hours and then kept at room temperature overnight. Chloroform (75 ml) is added to the stirred mixture and, after 10 minutes, the product is collected and washed with acetone to give 3.1 g of crude product. When the filtrate, concentrated and resuspended in acetone, is stirred with additional 2-amino-2-thiazoline (2.2 g) at room temperature overnight, another 2.5 g is isolated for a combined yield of 5.6 g (82%).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 5 hours
  3. customthe product is collected
  4. washwashed with acetone

Sources & evidence

ORD record
ord-719a7ddb9172448c83f5f21cbf1ee683
Source dataset
uspto-grants-1978_12
Patent number
US04128648

Linked notes

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