Water → HCID 19699487, compound

HRID 863100Notes

Reaction equation

HRID 863100 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 mL of THF was cooled to 0° C. and LAH (1.0M, 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-b45b1e06af464fdb828aaaad1a0052ef
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

Loading…