Triethylamine → HCID 683130, compound

HRID 567671Notes

Reaction equation

HRID 567671 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=O>C1(C)C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 762552-Amino-5-methylbenzoic acidHCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 683130HCID 683130, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Amino-5-methylbenzoic acid (0.5 g) and triethyl amine (10 ml) were mixed in dry toluene (20 ml). 2-Thienylcarbonyl chloride (1.07 g) was added dropwise under cooling and stirring. The mixture was subsequently heated to RT for 24 h, then heated to 80° C. for 1 h. After cooling on ice the precipitate was filtered off and the filtrate evaporated to dryness. The residue was partitioned between methylene chloride and potassium carbonate (2N), the organic layers separated, dried over magnesium sulfate and evaporated to dryness. The raw product was purified by column chromatography on silicagel using heptane/ethyl acetate as eluent.

Workup

  1. temperatureunder cooling
  2. temperatureheated to 80° C. for 1 h
  3. temperatureAfter cooling on ice the precipitate
  4. filtrationwas filtered off
  5. customthe filtrate evaporated to dryness
  6. customThe residue was partitioned between methylene chloride and potassium carbonate (2N)
  7. customthe organic layers separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customThe raw product was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-c74c5e42d35940c79b9fd7bef6a4404b
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Reaction notes

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