Bentazon → HCID 20334440, compound

HRID 1706784Notes

Reaction equation

HRID 1706784 reaction equation
[CH3:1][CH:2]([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)=O)[CH3:3].[CH2:17]([N:19]([CH2:23][CH3:24])[C:20](Cl)=[O:21])[CH3:18]>C(N(CC)CC)C>[CH2:17]([N:19]([CH2:23][CH3:24])[C:20]([N:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9](=[O:10])[N:4]([CH:2]([CH3:3])[CH3:1])[S:5]1)=[O:21])[CH3:18]

Participants

4

Reactant 2

HCID 2328BentazonHCID 6916Diethylcarbamoyl chloride

Product 1

HCID 20334440HCID 20334440, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner 12 g of 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide was caused to react with 7.28 g of diethylcarbamoyl chloride in the presence of 14 ml of triethylamine. The crude product was crystallized from methanol to afford 12.4 g of N,N-diethyl-3,4-dihydro-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carboxamide, m.p. 103°-104.5° C.

Workup

  1. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-b3e69d597c954f9f94bbbf09957ee091
Source dataset
uspto-grants-1980_06
Patent number
US04208514

Reaction notes

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