Triethylamine → HCID 14835024, compound

HRID 728423Notes

Reaction equation

HRID 728423 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH3:23])[CH2:20][NH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[Cl:31][CH2:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Cl:31][CH2:32][CH2:33][CH2:34][S:35]([NH:21][CH2:20][CH:19]([O:22][CH3:23])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 14992264HCID 14992264, compound

Product 1

HCID 14835024HCID 14835024, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.368 g (10.22 mM) of 3-hexadecyloxy-2-methoxypropylamine IVa3 in 35 ml of dichloromethane and 1.85 ml (13.29 mM) of triethylamine is added 1.99 g (11.24 mM) of 3-chloropropanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature for 4 hours and then heated for 30 minutes with stirring. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:1) mixture as an eluent. The product is recrystallized form methanol to give 4.15 g (8.827 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecyloxy-2-methoxypropane IIIa3 as a colorless powder in 86% yield.

Workup

  1. temperaturecooling
  2. temperatureheated for 30 minutes
  3. stirringwith stirring
  4. customAfter the solvent is evaporated
  5. customthe residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:1) mixture as an eluent
  6. customThe product is recrystallized form methanol

Sources & evidence

ORD record
ord-38cfa4a6637c4426800e3604b94798af
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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