Potassium Hydroxide → HCID 20532838, compound

HRID 1758882Notes

Reaction equation

HRID 1758882 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#N)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[BH4-].[Na+].[OH-].[K+].ClC[CH:20]1[CH2:22][CH2:21]1>C(O)C.C(Cl)(Cl)Cl.O>[CH:20]1([CH2:12][S:11][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 80013(Chloromethyl)cyclopropaneHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 20532838HCID 20532838, compoundYield 67.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 11.7 g (0.06 mole) of 2-nitro-4-thiocyanoaniline in 500 ml of absolute ethanol under nitrogen there is added 2.5 g (0.06 mole) of sodium borohydride in portions. The mixture is stirred at room temperature for 15 minutes and then refluxed for 15 minutes. The heating mantle is removed and 3.9 g (0.06 mole) of KOH in 25 ml of absolute ethanol is added. The mixture is stirred for 1 minute. A solution of 4.8 g (0.06 mole) of (chloromethyl) cyclopropane in 10 ml of absolute ethanol is added and the mixture is stirred at room temperature for 15 minutes then refluxed for 2 hours. Equal amounts of water and CHCl3 are added until 2 layers are formed. The organic layer is separated, dried (MgSO4), and the solvent removed in vacuo to give 9.1 g of an orange-red solid, m.p. 45°-47°.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThe heating mantle is removed
  3. stirringThe mixture is stirred for 1 minute
  4. stirringthe mixture is stirred at room temperature for 15 minutes
  5. temperaturethen refluxed for 2 hours
  6. customare formed
  7. customThe organic layer is separated
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c14543dd5acc401d9ebb1a9babd7f5d6
Source dataset
uspto-grants-1982_07
Patent number
USRE030990

Reaction notes

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