Triethylamine → HCID 58309271, compound

HRID 537638Notes

Reaction equation

HRID 537638 reaction equation
[CH3:1][N:2]([CH3:41])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:32]3[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=3)[O:14][C:13]3[C:15]4[C:20]([CH:21]=[C:22]([C:23]([O:25][CH2:26][CH2:27][OH:28])=[O:24])[C:12]=3[CH:11]=[CH:10]2)=[CH:19][CH:18]=[C:17]([N:29]([CH3:31])[CH3:30])[CH:16]=4)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:49](Cl)(=[O:52])[CH2:50][CH3:51]>C(Cl)Cl>[CH3:39][N:38]([CH3:40])[C:35]1[CH:36]=[CH:37][C:32]([C:9]2([C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:41])[CH3:1])=[CH:8][CH:7]=3)[O:14][C:13]3[C:15]4[C:20]([CH:21]=[C:22]([C:23]([O:25][CH2:26][CH2:27][O:28][C:49](=[O:52])[CH2:50][CH3:51])=[O:24])[C:12]=3[CH:11]=[CH:10]2)=[CH:19][CH:18]=[C:17]([N:29]([CH3:30])[CH3:31])[CH:16]=4)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 58309311HCID 58309311, compound

Product 1

HCID 58309271HCID 58309271, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2-bis(4-dimethylaminophenyl)-5-(2-hydroxyethoxycarbonyl)-9-dimethylamino-[2H]-naphtho[1,2-b]pyran (Example 9, Step 5) (0.045 g, 0.082 mmol) and triethylamine (0.05 ml) in dry DCM (5 ml) was added propionyl chloride in one portion (0.0075 g, 0.082 mmol) and the mixture stirred at RT for 30 minutes. The solvent was then evaporated in vacuo and the crude residue purified by column chromatography (silica gel, DCM/diethyl ether, 10:1), giving the pure product, 2,2-bis(4-dimethylaminophenyl)-5-(2-propionyloxy-ethoxycarbonyl)-9-dimethylamino-[2H]-naphtho[1,2-b]pyran (0.044 g, 89%).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe crude residue purified by column chromatography (silica gel, DCM/diethyl ether, 10:1)

Sources & evidence

ORD record
ord-b00b426392f54b78b0bf474f4ae0303b
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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