Sodium Carbonate → 2-Amino-4-bromobenzamide

HRID 1619341Notes

Reaction equation

HRID 1619341 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH4+].[Cl-].C[N:15](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 886912-Amino-4-bromobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 138055072-Amino-4-bromobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-4-bromobenzoic acid (1 g, 4.63 mmol), NH4Cl (1.8 g, 32.41 mmol), TBTU (1.5 g, 4.63 mmol) and diisopropylethylamine (1.2 g, 9.26 mmol) in DMF (30 mL) was stirred at room temperature overnight. Then the mixture was adjusted to pH 8.0 with saturated Na2CO3 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the desired yellow product. MS (ESI): 215, 217 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give the desired yellow product

Sources & evidence

ORD record
ord-3bf2fd7fae3b40418e647107ac3d1f29
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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