Dabco → HCID 54057117, compound

HRID 1973398Notes

Reaction equation

HRID 1973398 reaction equation
[OH:1][C:2]1[C:10]2[C:6](=[CH:7][S:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2].[CH3:40][N:41]=[C:42]=[O:43]>C1C=CC=CC=1>[N:9]1[S:8][CH:7]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][C:42](=[O:43])[NH:41][CH3:40])[C:10]=12

Participants

6

Reactant 4

HCID 9237DabcoHCID 93182-ethylhexanoic acid tin(II) saltHCID 12228Methyl IsocyanateHCID 214914432,1-Benzothiazol-7-ol

Product 1

HCID 54057117HCID 54057117, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.0 g. 7-hydroxy-2,1-benzisothiazole, 40 ml. dry benzene, and catalytic amounts of triethylenediamine and stannous octoate was added 2.5 g. methylisocyanate. After about five minutes at room temperature, yellow solid carbamate product crystallized from solution. The mixture was allowed to stand at room temperature overnight, then solvent and excess methylisocyanate were removed by evaporation on a rotatory evaporator. The solid residue was washed with hot hexane and isolated by suction filtration to give 2.6 g. yellow, microcrystalline 2,1-benzisothiazol-7-yl N-methylcarbamate, mp. 145°-148° (dec.) after recrystallization from benzene. This structure was confirmed by ir and nmr. The insecticidal activity of this material was determined exactly as described in Example 12, whereby 2,1-benzisothiazol-7-yl N-methylcarbamate (500 ppm. concentration) destroyed 100 percent of Mexican bean beetle larvae and bean aphids, four of five southern armyworms, and had no effect on two-spotted mites.

Workup

  1. customyellow solid carbamate product crystallized from solution
  2. waitto stand at room temperature overnight
  3. customsolvent and excess methylisocyanate were removed by evaporation on a rotatory evaporator
  4. washThe solid residue was washed with hot hexane
  5. customisolated by suction filtration
  6. customto give 2.6 g
  7. customyellow, microcrystalline 2,1-benzisothiazol-7-yl N-methylcarbamate, mp. 145°-148° (dec.) after recrystallization from benzene
  8. customdestroyed 100 percent of Mexican bean beetle larvae and bean aphids, four of five southern armyworms

Sources & evidence

ORD record
ord-eeab6f83f25145f5b8349ae7d3a75d6d
Source dataset
uspto-grants-1976_12
Patent number
US03997548

Reaction notes

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