Hydrochloric Acid → HCID 88463212, compound

HRID 1974798Notes

Reaction equation

HRID 1974798 reaction equation
[C:1]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=O)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(Cl)([Cl:28])=O.S(=O)=O.Cl>C(Cl)Cl>[C:1]([NH:20][CH2:21][CH2:22][C:23]([Cl:28])=[O:25])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24386Thionyl ChlorideHCID 58830700HCID 58830700, compound

Product 1

HCID 88463212HCID 88463212, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

61.3 g of N-oleoyl-β-alanine was dispersed in 200 ml of methylene chloride. Then, 24.8 g of thionyl chloride was added thereto within 10 minutes under stirring while maintaining the temperature of the mixture at 20° C. After the completion of the addition, the mixture was stirred at the same temperature for 30 minutes so as to complete the reaction. When the reaction solution thus obtained was analyzed by infrared spectroscopy, a peak at 1695 cm-1 due to carboxylic acid (--COOH) disappeared while a new peak due to acid chloride (--COCl) was formed at 1782 cm-1. These facts indicated that an acid chloride was obtained. Then, the methylene chloride employed as the solvent and side products (sulfur dioxide and hydrogen chloride) were distilled off from the reaction mixture under reduced pressure. Thus, 64.1 g of N-oleoyl-3-aminopropionic acid chloride was obtained.

Workup

  1. additionAfter the completion of the addition
  2. stirringthe mixture was stirred at the same temperature for 30 minutes so as
  3. customthe reaction
  4. customWhen the reaction solution thus obtained
  5. customwas formed at 1782 cm-1
  6. customwas obtained
  7. distillationwere distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-b750cecb894249e2a92be525472450dc
Source dataset
uspto-grants-1994_02
Patent number
US05284602

Reaction notes

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