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Acrylic Acid → N-[3-(Dimethylamino)propyl]-N-[(nonafluorobutyl)sulfonyl]-beta-alanine

HRID 129354
Notes
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Reaction equation

HRID 129354 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:6]([S:19]([NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(=[O:21])=[O:20])([C:9]([C:12]([C:15]([F:18])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C(OCCOCCO)CCC>O>[C:6]([S:19]([N:22]([CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[CH2:3][CH2:2][C:1]([OH:5])=[O:4])(=[O:20])=[O:21])([C:9]([C:12]([C:15]([F:16])([F:17])[F:18])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6581Acrylic Acid2×HCID 7108PhenothiazineHCID 8177Diethylene Glycol Monobutyl EtherHCID 1105581-Butanesulfonamide, N-[3-(dimethylamino)propyl]-1,1,2,2,3,3,4,4,4-nonafluoro-

Product 1

HCID 15251601N-[3-(Dimethylamino)propyl]-N-[(nonafluorobutyl)sulfonyl]-beta-alanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
125 °C

Procedure

An acrylic acid Michael addition reaction was then run according to the general procedure given in U.S. Pat. No. 5,144,069 (Stern et al.). 50 g (0.12 mole) of the purified C4F9SO2N(H)C3H6N(CH3)2, 16.4 g (0.23 mole) of acrylic acid and 0.2 g of phenothiazine (free radical polymerization inhibitor) were added to a 250-mL three-neck flask equipped with an air stirrer and thermometer. The resulting mixture was heated to 125° C. and was allowed to react for 6 hours. After this reaction period, a positive solubility check of the product in water of pH 7 indicated that the Michael addition reaction was essentially complete. While still mixing, a solvent blend of 18 g of diethylene glycol monobutyl ether and 42 g of deionized water was added and the mixture was allowed to cool to room temperature. The water solubility test was run again with the same positive result, showing good conversion to the desired Michael addition product, C4F9SO2N(C2H4COOH)C3H6 (CH3)2.

Workup

  1. customequipped with an air stirrer
  2. customto react for 6 hours
  3. customAfter this reaction period
  4. additionWhile still mixing
  5. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-6db07f2762984316b90d6f5c14a17a70
Source dataset
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05468353

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes