Hydrochloric Acid → HCID 21404066, compound

HRID 972434Notes

Reaction equation

HRID 972434 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15](Cl)(=[O:17])=[O:16])=[CH:7][CH:6]=1)(=O)C.[CH2:19]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C.[OH-].[K+].Cl>CCOCC.O.C(#N)C>[CH2:32]([N:31]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[S:15]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([OH:4])=[CH:6][CH:7]=1)(=[O:16])=[O:17])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 18157DidodecylamineHCID 214040784-(Chlorosulfonyl)naphthalen-1-yl acetate

Product 1

HCID 21404066HCID 21404066, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 18.1 g (0.063 mole) 1-acetoxy-4-naphthalenesulfonyl chloride, 22.4 g (0.063 mole) N,N-didodecylamine, 25 ml (18.1 g, 0.18 mole) triethylamine, and 200 ml acetonitrile was stirred at room temperature for 18 hrs. The mixture was diluted with ether and poured into water. The ether layer was separated, dried, and concentrated to 16.1 g of an amber oil, which was dissolved in 100 ml ethanol. To the solution was added 1.50 g (0.027 mole) potassium hydroxide; the mixture was stirred at room temperature for 2 days, acidified with hydrochloric acid, and diluted with water. The mixture was extracted with ether, and the extract was concentrated to 30.7 g of an amber oil, which partially crystallized.

Workup

  1. customThe ether layer was separated
  2. customdried
  3. concentrationconcentrated to 16.1 g of an amber oil, which
  4. dissolutionwas dissolved in 100 ml ethanol
  5. stirringthe mixture was stirred at room temperature for 2 days
  6. extractionThe mixture was extracted with ether
  7. concentrationthe extract was concentrated to 30.7 g of an amber oil, which
  8. custompartially crystallized

Sources & evidence

ORD record
ord-e250f05f53624c4dbb883b29fb802961
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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