Phenol → HCID 20143059, compound

HRID 649316Notes

Reaction equation

HRID 649316 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=2[S:5][CH2:4][C:3]1=[O:13].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.S(Cl)(Cl)(=O)=O>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=2[S:5][CH:4]([C:17]2[CH:18]=[CH:19][C:14]([OH:20])=[CH:15][CH:16]=2)[C:3]1=[O:13]

Participants

5

Reactant 2

HCID 996PhenolHCID 18952076HCID 18952076, compound

Product 1

HCID 20143059HCID 20143059, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24648Sulfuryl chlorideSolvent

Procedure

To a stirred solution of 3,4-dihydro-4,7-dimethyl-3-oxo-2H-1,4-benzothiazine (11.0 g) in methylene chloride (50 ml), sulfuryl chloride (4.8 ml) is added under ice-cooling. After the addition, the mixture is stirred for 15 minutes under ice-cooling. Phenol (7.0 g) is added to the mixture, and the mixture is stirred for 45 minutes and concentrated in vacuo. Ether is added to the residue and the separated crystals are collected by filtration to give 11.3 g (69.4%) of the titled compound.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. temperaturecooling
  4. stirringthe mixture is stirred for 45 minutes
  5. concentrationconcentrated in vacuo
  6. additionEther is added to the residue
  7. filtrationthe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-7c4d15b3578c4326b6677c619e89b232
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

Loading…