Triethylamine → HCID 19766982, compound

HRID 1591409Notes

Reaction equation

HRID 1591409 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][C:21](O)=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11]1)(=[O:8])=[O:7].S(Cl)(Cl)=O.[NH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][C:21]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=3)=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11]1)(=[O:8])=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12082Methyl 4-aminobenzoateHCID 24386Thionyl ChlorideHCID 19766977HCID 19766977, compound

Product 1

HCID 19766982HCID 19766982, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1.51 g of 6-(2-thienyl)sulfonylamino-5,6,7,8-tetrahydronaphthalene-2-acetic acid, 20 ml of methylene chloride, one drop of dimethylformamide and 3.3 ml of thionyl chloride is refluxed for 2 hours, and the solvent is removed to give yellow oil. A solution of the oil in 20 ml of methylene chloride is added dropwise to a solution of 1.30 g of methyl 4-aminobenzoate and 1.31 g of triethylamine in 15 ml of methylene chloride under stirring at room temperature. After the mixture is stirred overnight, the solvent is distilled off. Ethyl acetate and 10% hydrochloric acid are added to the residue, and the organic layer is separated therefrom, washed, dried and evaporated to remove the solvent. The resulting solid is recrystallized from a mixture of tetrahydrofuran and isopropyl ether to give 1.58 g of methyl 4-{[6-(2-thienyl)sulfonylamino-5,6,7,8-tetrahydronaphthalene-2-yl]acetylamino}benzoate as pale yellow crystals.

Workup

  1. temperatureis refluxed for 2 hours
  2. customthe solvent is removed
  3. customto give yellow oil
  4. stirringAfter the mixture is stirred overnight
  5. distillationthe solvent is distilled off
  6. additionEthyl acetate and 10% hydrochloric acid are added to the residue
  7. customthe organic layer is separated
  8. washwashed
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. customThe resulting solid is recrystallized from a mixture of tetrahydrofuran and isopropyl ether

Sources & evidence

ORD record
ord-c0a88740c26d40119724d44f7d1853d5
Source dataset
uspto-grants-1993_04
Patent number
US05206428

Reaction notes

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