Phosgene → HCID 20209820, compound

HRID 542250

Reaction equation

HRID 542250 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[N:11]([CH3:22])[S:12](=[O:21])(=[O:20])[C:13]2[CH:19]=[CH:18][S:17][C:14]=2[C:15]=1[OH:16])=[O:9].C(N(CC)CC)C.[C:30](Cl)([Cl:32])=[O:31]>C1(C)C=CC=CC=1>[ClH:32].[CH3:22][N:11]1[C:10]2[C:8](=[O:9])[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:30](=[O:31])[O:16][C:15]=2[C:14]2[S:17][CH:18]=[CH:19][C:13]=2[S:12]1(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 54677971Tenoxicam

Product 1

HCID 20209820HCID 20209820, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3.37 g. (10 mmole) N-(2-pyridyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (tenoxicam) in 150 ml. toluene under nitrogen is added 1.01 g. (10 mmole) triethylamine and the mixture is cooled to 0° C. The cold solution is then added dropwise to a solution of 1.0 g. (10 mmole) phosgene in 50 ml. toluene at -70° C. over 45 minutes and stirring is continued at -70° to -60° C. for an additional 30 minutes. The reaction mixture is allowed to warm to room temperature and stirred for an hour. The solvent is evaporated in vacuo, the residue triturated with acetone and filtered to obtain the desired product which is purified by recrystallization, e.g., from acetine, ethanol or chloroform.

Workup

  1. additionThe cold solution is then added dropwise to a solution of 1.0 g
  2. stirringstirred for an hour
  3. customThe solvent is evaporated in vacuo
  4. customthe residue triturated with acetone
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b971470fe1ed433b816949f64be0e5c7
Source dataset
uspto-grants-1987_04
Patent number
US04656265

Linked notes

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