Bentazon → 1-[5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl]-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide

HRID 1759297Notes

Reaction equation

HRID 1759297 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][S:5]1(=[O:16])=[O:15])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:30]([O-:32])=[O:31])=[C:25]([CH:29]=1)[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:17][C:18]1[CH:36]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:34]=[CH:33][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:30]([O-:32])=[O:31])=[C:25]([CH:29]=1)[C:26]([N:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[S:5]1(=[O:15])=[O:16])=[O:27]

Participants

5

Reactant 2

HCID 2328BentazonHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 130379681-[5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl]-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxideYield 48%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (2.4 g, 0.01 mole) and tricthylamine (1.1 g, 0.011 mole) in a mixture of toluene (100 ml) and chloroform (100 ml) was added 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole). The reaction was heated for 24 hours and then the solvent was removed. The residue was taken back up into chloroform and extracted three times with sodium hydroxide and finally with water. The organic solution was dried and evaporated to give 2.8 g of an oil which was triturated with petroleum ether to give a solid which was recrystallized from chloroform-petroleum ether to give a white solid, mp 125°-8° C.

Workup

  1. temperatureThe reaction was heated for 24 hours
  2. customthe solvent was removed
  3. extractionextracted three times with sodium hydroxide
  4. customThe organic solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-eedcf819f34b4f90832152afe797dadd
Source dataset
uspto-grants-1982_07
Patent number
US04340417

Reaction notes

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