Ammonia → HCID 19864114, compound

HRID 1199888Notes

Reaction equation

HRID 1199888 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:16])[C:13](=[N:14]O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][S:5]1.N>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[NH2:14][CH:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][S:5][C:4]1([CH3:16])[CH3:3]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 86743768HCID 86743768, compound

Product 1

HCID 19864114HCID 19864114, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

25.3 g of sodium borohydride in 435 ml of 1,2-dimethoxyethane are placed under a nitrogen atmosphere. 36.9 ml of titanium tetrachloride are added dropwise thereto at a temperature of from +15° to +18° C. The mixture is stirred for 3 hours at a temperature below +20° C. and then, at from +14° to +16° C., a solution of 33.0 g of 3,3-dimethylisothiochroman-4-oneoxime in 135 ml of 1,2-dimethoxyethane is added dropwise thereto. After stirring for 16 hours at room temperature, the mixture is poured onto ice-water and rendered basic with 30% aqueous ammonia solution. The mixture is then extracted twice with ether. The ether phases are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation. Distillation of the residue yields 16.7 g of 4-amino-3,3-dimethylisothiochroman in the form of a colourless liquid having a boiling point of +80° C. at 0.06 mbar.

Workup

  1. customof from +15° to +18° C
  2. stirringAfter stirring for 16 hours at room temperature
  3. additionthe mixture is poured onto ice-water
  4. extractionThe mixture is then extracted twice with ether
  5. washThe ether phases are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-e52d997084e947ba9b913374940d36ad
Source dataset
uspto-grants-1990_02
Patent number
US04904300

Reaction notes

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