Triethylamine → HCID 3073932, compound

HRID 274748Notes

Reaction equation

HRID 274748 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[S:14][CH2:13][CH2:12][CH2:11]2.[NH2:16][CH:17]1[CH2:22][O:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:19]=2[CH2:18]1.C(N(CC)CC)C>CN(C)C=O>[CH3:28][O:27][C:26]1[C:19]2[CH2:18][CH:17]([NH:16][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:15]=3[S:14][CH2:13][CH2:12][CH2:11]4)[CH2:22][O:21][C:20]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139289485-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amineHCID 15295830HCID 15295830, compound

Product 1

HCID 3073932HCID 3073932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 1.6 g (5.58 mmol) of 8-[(3-bromopropyl)oxy]thiochroman, 1 g (5.58 mmol) of 3-amino-5-methoxy-dihydro-[2H]-benzo[b]pyran and 1.69 g (16.74 mmol) of triethylamine are dissolved in 20 cm3 of dimethylformamide. The mixture is kept at room temperature for 24 hours. The solvent is evaporated off. The residue is taken up in H2O and extracted with methylene chloride. The product is dried over MgSO4. After evaporation, the product is purified over a flash silica column. Eluant: methanol/CH2Cl2 5: 95. The title compound is obtained (yellow oil).

Workup

  1. customThe solvent is evaporated off
  2. extractionextracted with methylene chloride
  3. dry with materialThe product is dried over MgSO4
  4. customAfter evaporation
  5. customthe product is purified over a flash silica column

Sources & evidence

ORD record
ord-f0a78a81bfad4e47907e26d03d533060
Source dataset
uspto-grants-1995_02
Patent number
US05389668

Reaction notes

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