Bentazon → HCID 20334436, compound

HRID 1706783Notes

Reaction equation

HRID 1706783 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:16])=[O:15])[CH3:3].C[C:18](C)([O-:20])C.[K+].Cl[C:24](OC)=[S:25]>C(#N)C>[CH3:3][CH:2]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([C:18](=[O:20])[S:25][CH3:24])[S:5]1(=[O:16])=[O:15])[CH3:1]

Participants

5

Reactant 3

HCID 2328BentazonHCID 554404Methyl chloromethanethioateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20334436HCID 20334436, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

To 200 ml of acetonitrile was added 24 g (0.1 mole) of 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and 11.8 g of potassium t-butoxide. The mixture was heated to reflux, cooled to 50° C. and 12.6 g (0.114 mole) of methyl chlorothioformate in 100 ml of acetonitrile was added over a 0.5 hour period. The temperature was maintained at 50°-52 C. Stirring was continued at 50° C. overnight. The mixture was cooled, filtered, and the solvent removed from the filtrate in vacuo. The residual solid was washed with 3-50 ml-portions of methanol to afford 21.7 g of analytically pure S-methyl 3,4-dihydro-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carbothioate-2,2-dioxide, m.p. 125°-127° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe temperature was maintained at 50°-52 C
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customthe solvent removed from the filtrate in vacuo
  7. washThe residual solid was washed with 3-50 ml-portions of methanol

Sources & evidence

ORD record
ord-62d93c11e53b4c3cb06a681eedc59c38
Source dataset
uspto-grants-1980_06
Patent number
US04208514

Reaction notes

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