Formaldehyde → HCID 53932913, compound

HRID 1578112Notes

Reaction equation

HRID 1578112 reaction equation
[CH2:1]=O.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23](=[O:24])[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[S:20]2(=[O:30])=[O:29])[CH2:15][CH2:14]1>CO>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:1][N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[S:20]3(=[O:29])=[O:30])[CH2:17][CH2:18]2)=[CH:4]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 798IndoleHCID 705454252-(Piperid-4-yl)-1,2-benzisothiazolin-3-one-1,1-dioxide hydrochloride

Product 1

HCID 53932913HCID 53932913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Formaldehyde (0.4 cm3, 40% aqu.soln.) was added to a mixture of indole (0.6 g, 0.005 mol), 2-(piperid-4-yl)-1,2-benzisothiazoline-3-one-1,1-dioxide, hydrochloride (1.5 g, 0.005 mol) and methanol (10 cm3). The mixture was warmed sufficiently to give a clear solution and then allowed to stand without further heating for 2 hours. The clear solution was then evaporated, and the residual water removed by successive evaporation of the residue with ethanol to give a gum. The gum was dissolved in methanol and allowed to stand in ice whereupon the crystalline title compound separated (1.7 g, 79%) as the hydrochloride. Recrystallisation twice from aqueous methanol (80% methanol) gave 1.3 g of the title compound as the hydrochloride hemihydrate, m.p. 214°-215° C.

Workup

  1. temperatureThe mixture was warmed sufficiently
  2. customto give a clear solution
  3. temperaturewithout further heating for 2 hours
  4. customThe clear solution was then evaporated
  5. customthe residual water removed by successive evaporation of the residue with ethanol
  6. customto give a gum

Sources & evidence

ORD record
ord-8b600960653a468d99739a7be9f6d4bc
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

Loading…