Hydrochloric Acid → N-[4-(hexadecylamino)benzoyl]-2-aminoethanesulfonic acid

HRID 2163789

Reaction equation

HRID 2163789 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].FC(F)(F)C([N:12]([C:29]1[CH:44]=[CH:43][C:32]([C:33](ON2C(=O)CCC2=O)=[O:34])=[CH:31][CH:30]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=O.[OH-].[Na+].Cl>O.C(O)C.C(N(CC)CC)C>[CH2:13]([NH:12][C:29]1[CH:30]=[CH:31][C:32]([C:33]([NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])=[O:34])=[CH:43][CH:44]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1123TaurineHCID 14798Sodium HydroxideHCID 20437360N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide

Product 1

HCID 20437369N-[4-(hexadecylamino)benzoyl]-2-aminoethanesulfonic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2.50 g. of taurine and 5.6 ml. of triethylamine in 22.5 ml. of water is added 5.55 g. of N-[p-(2,2,2-trifluoro-N-hexadecylacetamido)benzoyloxy]succinimide as a solution in 45 ml. of ethanol. After 24 hours, the mixture is treated with 20 ml. of 2.0M sodium hydroxide and 25 ml. of water. After stirring for 10 min., the mixture is acidified with dilute hydrochloric acid, and the crude product is collected by filtration. Recrystallization affords the title compound as a white solid, m.p. 190°-220° C.

Workup

  1. additionthe mixture is treated with 20 ml
  2. filtrationthe crude product is collected by filtration
  3. customRecrystallization

Sources & evidence

ORD record
ord-f377ed7c16e14487b3f13d1ce25884d8
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Linked notes

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