Heptane → Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-, methyl ester

HRID 1635694Notes

Reaction equation

HRID 1635694 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.CCCCCCC.C(=O)(O)[O-].[K+].[CH2:38]([S:42](Cl)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41]>O>[CH2:38]([S:42]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:8]([O:10][CH3:11])=[O:9])=[CH:24][CH:25]=1)(=[O:44])=[O:43])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 754301-Butanesulfonyl chloride2×HCID 112569Tetradecanoic acid, 2-(4-aminophenoxy)-, methyl esterHCID 516893Potassium Bicarbonate2×

Product 1

HCID 18676574Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A heel was created batchwise by charging 142.2 g (0.41 moles) of methyl 2-[4-aminophenoxy]tetradecanoate (the amine), 267.7 g of heptane, 45.7 g (0.46 moles) of potassium bicarbonate, and 119.7 g of deionized water. The two-phase mixture was stirred with high agitation (800-900 rpm) and heated to 55° C-60° C. at which point 71.4 g of butanesulfonyl chloride was added over approximately 1 hour. After stirring for one hour, the composition of the assay of the product in the upper organic phase was 98.9%. At this point, continuous feeds into the reactor system, which consists of two reactors and a processing tank, were started to provide six hours of residence time in the two reactors. The feed rates were: 1.46 g/min (2.63 mmoles/min) of the amine solution (63 wt % in heptane), 0.45 g/min (2.87 mmoles/min) of the butanesulfonyl chloride, and 1.42 g/min (2.87 mmoles/min) of a 20 wt % potassium bicarbonate solution.

Workup

  1. temperatureheated to 55° C-60° C. at which
  2. additionwas added over approximately 1 hour
  3. stirringAfter stirring for one hour
  4. customto provide six hours of residence time in the two reactors

Sources & evidence

ORD record
ord-c700e60607f84ee388e73afcf3e2abd1
Source dataset
uspto-grants-2003_01
Patent number
US06509500B2

Reaction notes

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