Thionyl Chloride → HCID 20063978, compound

HRID 359824Notes

Reaction equation

HRID 359824 reaction equation
S(Cl)([Cl:3])=O.[O:5]1[CH2:9][CH2:8][N:7]=[C:6]1[C:10]1[CH:31]=[CH:30][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[O:26][N:25]=[C:24]([CH3:27])[C:23]=2[CH2:28]O)=[CH:12][CH:11]=1>C(Cl)Cl>[Cl:3][CH2:28][C:23]1[C:24]([CH3:27])=[N:25][O:26][C:22]=1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:13]1[CH:30]=[CH:31][C:10]([C:6]2[O:5][CH2:9][CH2:8][N:7]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20064065HCID 20064065, compound

Product 1

HCID 20063978HCID 20063978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.1 ml of thionyl chloride in 5.0 ml of methylene dichloride cooled in an ice-bath was added over a 30 minute period a suspension of 5 g of 5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-methyl-4-isoxazolemethanol (Example 29b) in 20 ml of methylene dichloride. The reaction mixture was stirred at 0° C. for 2 hours and then at room temperature for 3 hours. The solvent was then removed in vacuo and the residue triturated with ether. The solid product was collected and recrystallized from acetonitrile to give 4.5 g of 4-chloromethyl-5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole in the form of its monohydrochloride salt, tan solid, m.p. 103°-104° C.

Workup

  1. additionwas added over a 30 minute period
  2. waitat room temperature for 3 hours
  3. customThe solvent was then removed in vacuo
  4. customthe residue triturated with ether
  5. customThe solid product was collected
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ec87a16ee46f4fcaa0ebba0f67813f99
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

Loading…