Triethylamine → HCID 66849352, compound

HRID 1191318Notes

Reaction equation

HRID 1191318 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35](Cl)=[O:36]>ClCCl.CN(C1C=CN=CC=1)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:35](=[O:36])[CH2:34][C:30]2[S:29][CH:33]=[CH:32][CH:31]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chloride2×HCID 66849502HCID 66849502, compound

Product 1

HCID 66849352HCID 66849352, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-bromo-2-[(4-methoxybenzyl)amino]benzoate (2.0 g, 5.7 mmol) in dichloromethane (0.50 M, 11 mL) at room temp were added triethylamine (1.6 mL, 11 mmol) and 2-thiophenylacetyl chloride (1.1 g, 6.9 mmol), followed by addition of DMAP (35 mg, 5.0 mol %). The reaction was left stirring overnight. Additional portions of 2-thiophenylacetyl chloride were added until the complete consumption of starting material was observed. The crude reaction mixture was poured in neutral water (100 mL). The product was extracted with dichloromethane (3×50 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo to furnish methyl 5-bromo-2-[(4-methoxybenzyl)(thiophen-2-ylacetyl)amino]benzoate as an orange oil. Used without further purification. LCMS (M+1)=473.7.

Workup

  1. waitThe reaction was left
  2. customThe crude reaction mixture
  3. extractionThe product was extracted with dichloromethane (3×50 mL)
  4. extractionThe combined organic extractions
  5. dry with materialwere dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d84ce737181c43d9a8b3dfa8c065f2b3
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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