HCID 13101053, compound → HCID 13101052, compound

HRID 261900Notes

Reaction equation

HRID 261900 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[S:8])=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1.ClC1C=CC2=C(NC(C)CCCN(CC)CC)SN=C2C=1>C(O)CCCCCCC>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[S:8])=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1

Participants

4

Reactant 2

HCID 13101053HCID 13101053, compoundHCID 21321574HCID 21321574, compound

Product 1

HCID 13101052HCID 13101052, compoundYield 326.4%

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent

Procedure

Starting with 1030 g. (2.61 moles) of 4-chloro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrothiobenzamide hydrochloride, the above procedure was repeated except that after the addition was complete the reaction mixture was stirred 4.5 hours without cooling; then treated with 150 ml. of n-octanol and stirred overnight at room temperature. The product was isolated as described above to give 715 g. of 6-chloro-3-[4-(diethylamino)-1-methylbutylamino]-2,1-benzisothiazole. A similar run starting with 3,360 g. (8.52 moles) of 4-chloro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrothiobenzamide produced 1,915 g. of product.

Workup

  1. additionafter the addition
  2. temperaturewithout cooling
  3. additionthen treated with 150 ml
  4. customThe product was isolated
  5. customto give 715 g

Sources & evidence

ORD record
ord-aefa6592c879440ea90b5dd73a2d23c2
Source dataset
uspto-grants-1979_05
Patent number
US04152518

Reaction notes

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