Water → HCID 19699487, compound

HRID 1735910Notes

Reaction equation

HRID 1735910 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]=[N:17]O)[NH:13][C:12]1=[S:19].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].O>C1COCC1.C(OCC)(=O)C>[NH2:17][CH2:16][C:14]1[NH:13][C:12](=[S:19])[N:11]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 73649606HCID 73649606, compound

Product 1

HCID 19699487HCID 19699487, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehyde oxime (0.158 g, 0.58 mmol), prepared as in Example 22, in 20 nil of THF was cooled to 0° C. and LAH (1.0 M, 1.16 mL, 1.16 mmol) in THF was added slowly. The mixture was stirred at 0° C. for 1 hour and then saturated ammonium chloride, water and ethyl acetate were added. The aqueous layer was separated and extracted with ethyl acetate. The combined ethyl acetate was dried over magnesium sulfate and concentrated by evaporation. Purification of the residue by flash chromatography (elution: 3-10% methanol/methylene chloride) gave 4-aminomethyl-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione, m.p. 197°-200° C.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate was dried over magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customPurification of the residue
  6. washby flash chromatography (elution: 3-10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-5a73660398eb4473a8cc4586534f1ca6
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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