Hydrochloric Acid → HCID 53668196, compound

HRID 1395037Notes

Reaction equation

HRID 1395037 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[C:6](Cl)=[N:5][S:4][N:3]=1.[OH:10][C:11]1[CH:21]=[CH:20][C:14]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+].Cl>O>[C:17]([CH:16]=[CH:15][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:6]2[C:7](=[O:8])[C:2]([Cl:1])=[N:3][S:4][N:5]=2)=[CH:21][CH:20]=1)([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3224-Coumaric acidHCID 14798Sodium HydroxideHCID 3540263,5-Dichloro-4H-1,2,6-thiadiazin-4-one

Product 1

HCID 53668196HCID 53668196, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 14.6 grams (0.08 mole) of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one in 350 ml of water was added dropwise a previously prepared solution of 13.1 grams (0.08 mole) of p-hydroxycinnamic acid in 80 ml of aqueous 1 N sodium hydroxide. The reaction mixture was stirred for 2 hours at ambient temperature, then acidified with aqueous 6 N hydrochloric acid. A yellow precipitate was collected by vacuum filtration and washed with water, then dried for 5 hours/50° C. The solid was triturated with hot ethanol and collected by vacuum filtration, to give 23.3 grams (93.8%) of 3-[4-(2-carboxyethenyl)phenoxy]-5-chloro-4H-1,2,6-thiadiazin-4-one; m.p. >280° C. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. filtrationA yellow precipitate was collected by vacuum filtration
  2. washwashed with water
  3. customdried for 5 hours/50° C
  4. customThe solid was triturated with hot ethanol
  5. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-006ec02776744983a2175803426e2a7b
Source dataset
uspto-grants-1980_05
Patent number
US04201780

Reaction notes

Loading…