Hydrochloric Acid → HCID 178443409, compound

HRID 1581080Notes

Reaction equation

HRID 1581080 reaction equation
O.[OH:2]C1C=CC([N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=O)C(N)=N)=CC=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O)[C:29]([NH2:31])=[NH:30])=[CH:24][CH:23]=1.[ClH:40]>>[OH2:2].[ClH:40].[OH:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([N-:9][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:13][CH2:14][CH2:15][CH3:16])=[O:39])[C:29]([NH2:31])=[NH:30])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131710017HCID 131710017, compound

Product 1

HCID 178443409HCID 178443409, compoundYield 60.8%

Procedure

2.7 g of ε-(N-p-hydroxyphenylguanidino)caproic acid hemihydrate was dissolved in dilute hydrochloric acid and concentrated under reduced pressure. The residue was dissolved in 30 ml of N,N-dimethylformamide and to the solution kept at 0° to 5°C was added dropwise 0.96 ml of ethylchloroformate and then 1.39 ml of triethylamine. After the mixture was stirred for 15 minutes, 1.6 g of n-decylamine was added dropwise to the mixture at 0° to 5°C. Thereafter, the reaction was carried out in the same manner as in Example 1. The resultant reaction mixture was concentrated under reduced pressure and cold 1N sodium hydroxide was added to the residue to separate precipitated oily substance. The precipitated oily substance was washed with ether and extracted with chloroform after being turned acidic by addition of hydrochloric acid. The chloroform layer was washed with water and dried with sodium sulfate, followed by concentration. Recrystallization of the residue from chloroformether gave 2.8 g of ε-(N-p-hydroxyphenylguanidino) caproyl-n-decyl amide hydrochloride monohydrate having a melting point of 73° to 75°C. The yield was 60.8%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 30 ml of N,N-dimethylformamide and to the solution
  3. customkept at 0° to 5°C
  4. additionwas added dropwise 0.96 ml of ethylchloroformate
  5. addition1.6 g of n-decylamine was added dropwise to the mixture at 0° to 5°C
  6. customThe resultant reaction mixture
  7. concentrationwas concentrated under reduced pressure and cold 1N sodium hydroxide
  8. additionwas added to the residue
  9. customto separate
  10. customprecipitated oily substance
  11. washThe precipitated oily substance was washed with ether
  12. extractionextracted with chloroform
  13. additionafter being turned acidic by addition of hydrochloric acid
  14. washThe chloroform layer was washed with water
  15. dry with materialdried with sodium sulfate
  16. concentrationfollowed by concentration
  17. customRecrystallization of the residue from chloroformether

Sources & evidence

ORD record
ord-89507d8c76884ad6b27f2160375c3cd9
Source dataset
uspto-grants-1976_01
Patent number
US03935266

Reaction notes

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