Hydrochloric Acid → HCID 21472159, compound

HRID 2294805Notes

Reaction equation

HRID 2294805 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[Cl:17][C:18]1[CH:19]=[C:20]([NH:24][CH2:25][C:26](O)=[O:27])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.ClCC(OCC)=O.Cl>O1CCCC1>[Cl:17][C:18]1[CH:19]=[C:20]([N:24]2[CH2:25][C:26](=[O:27])[N:14]([S:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)(=[O:13])=[O:12])[C:15]2=[O:16])[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 37803192-[(3-chlorophenyl)amino]acetic AcidHCID 13629361Naphthalene-2-sulfonyl isocyanate

Product 1

HCID 21472159HCID 21472159, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In accordance with the synthesis process (B), 1.0 g (81%, 3.49 mmol) of 2-naphthalenesulfonyl isocyanate was added to a solution of 647 mg (3.49 mmol) of N-3-chlorophenylaminoacetic acid in 50 ml of tetrahydrofuran at room temperature, and the resultant mixture was stirred for 16 hours. After completion of the reaction, the liquid reaction mixture was cooled to 0° C. and added with 881 mg (8.72 mmol) of triethylamine and 417 mg (3.84 mmol) of ethyl chloroacetate, followed by stirring at 0° C. for 1 hour. After completion of the reaction, the liquid reaction mixture was added with 20 ml of 1N hydrochloric acid and 30 ml of saturated saline and subjected to extraction with ethyl acetate. After washing the resultant extract with water, it was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus-obtained crude product was purified by column chromatography on silica gel (hexane/ethyl acetate=3:1) and subjected to crystallization from hexane/ethyl acetate, thereby obtaining 324 mg (0.81 mmol) of the title compound as white crystals (yield: 23.2%).

Workup

  1. customAfter completion of the reaction
  2. customthe liquid reaction mixture
  3. customAfter completion of the reaction
  4. customthe liquid reaction mixture
  5. extractionsubjected to extraction with ethyl acetate
  6. washAfter washing the resultant
  7. extractionextract with water, it
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe thus-obtained crude product
  11. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=3:1)
  12. customsubjected to crystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-8b22a579d00f49d0a0d620a1fa7dcdc6
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

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