Triethylamine → HCID 89767843, compound

HRID 591480Notes

Reaction equation

HRID 591480 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[CH:10][C:5]=2[S:4][C:3]=1[C:21]([OH:23])=O.CC[N:26]=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].O>[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[CH:10][C:5]=2[S:4][C:3]=1[C:21]([NH2:26])=[O:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 89768127HCID 89768127, compound

Product 1

HCID 89767843HCID 89767843, compoundYield 102.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzothiophene-2-carboxylic acid (190.4 mg) in DMF (dry) (4.9 mL) were added HOBt ammonia complex (112 mg), EDCI (141 mg) and triethylamine (0.205 mL). The mixture was stirred at room temperature overnight. The mixture was diluted with saturated aqueous NaHCO3 and water. The precipitate was collected by filtration, and washed with water and hexane to give the title compound (195 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and hexane

Sources & evidence

ORD record
ord-5ecfcf7d506f4c22bb65cfee9f004db5
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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