Water → N-acetyl-5-methylthio-2-indanamine

HRID 1701340Notes

Reaction equation

HRID 1701340 reaction equation
[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:14](Cl)(=O)=O)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].O.[CH3:19]I.C[O-].[Na+]>C(O)(=O)C.Cl>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:14][CH3:19])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 203478562-Acetamido-2,3-dihydro-1h-indene-5-sulfonyl chloride

Product 1

HCID 20347848N-acetyl-5-methylthio-2-indanamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
75 °C

Procedure

5.6 g. of N-acetyl-5-chlorosulfonyl-2-indanamine (0.02 mole) (as prepared in Example 3) is dissolved in acetic acid (50 ml.), warmed to 75° C., and 19 g. of stannous chloride (0.1 mole) in concentrated hydrochloric acid (20 ml.) is added. An exotherm occurs. When the reduction is complete the mixture is cooled to 25° C. and poured into water. The N-acetyl-5-mercapto-2-indanamine is filtered and suspended in methanol (50 ml.) under a nitrogen atmosphere. 5.7 g. of methyl iodide (0.04 mole) and 1.1 g. of sodium methoxide (0.02 mole) are added and the mixture is stirred for one hour. The mixture is filtered, evaporated and the residue purified by chromatography to give N-acetyl-5-methylthio-2-indanamine which is hydrolyzed following the procedure of Example 3 to give 5-methylthio-2-indanamine.

Workup

  1. temperatureis cooled to 25° C.
  2. filtrationThe N-acetyl-5-mercapto-2-indanamine is filtered
  3. filtrationThe mixture is filtered
  4. customevaporated
  5. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-55207bb5a134494b89423c40f2f0a924
Source dataset
uspto-grants-1980_03
Patent number
US04192888

Reaction notes

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