Sodium Carbonate → HCID 58574198, compound

HRID 1619301Notes

Reaction equation

HRID 1619301 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][NH:13][C:14]([CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1)=O.O=S(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[N:13]([CH3:12])[C:14]([CH:16]3[CH2:20][CH2:19][O:18][CH2:17]3)=[N:1]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 886912-Amino-4-bromobenzoic acidHCID 20784596HCID 20784596, compound

Product 1

HCID 58574198HCID 58574198, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 2-amino-4-bromobenzoic acid (349 mg, 1.62 mmol), N-methyltetrahydrofuran-3-carboxamide (190 mg, 1.47 mmol), SOCl2 (0.13 mL, 1.76 mmol) and toluene (10 mL) was stirred at 80° C. for 5 h, and Na2CO3 aqueous solution was added after the mixture was cooled to room temperature. The water layer was extracted with ethyl acetate (3×10 mL) and the combined organic layers were dried over Na2SO4, filtered, and evaporated to give the desired product, which was directly used for the next step. MS (ESI): 309, 311 (MH+).

Workup

  1. temperaturewas cooled to room temperature
  2. extractionThe water layer was extracted with ethyl acetate (3×10 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2217f54a618a4a5db64e14fb1f03bfe9
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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