Dimethylformamide → HCID 86659807, compound

HRID 1846314Notes

Reaction equation

HRID 1846314 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.CN(C=O)C>O>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([Br:14])=[CH:16][CH:17]=1)=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78074-BromoanilineHCID 5175353-Chloroisatoic anhydride

Product 1

HCID 86659807HCID 86659807, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 8-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (0.80 g, 4.05 mmol) and 4-bromoaniline (0.70 g, 4.05 mmol) with anhydrous DMF (1 mL) was heated at 130° C. for 2 hours. Water (50 mL) was added, and the product was extracted with ethyl acetate (200 mL). The organic phase was separated, washed with water (100 mL), brine (100 mL) and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo, and the crude material was washed with ether, to give 2-amino-N-(4-bromophenyl)-3-chlorobenzamide as an off-white solid. Yield 1.17 g (89%).

Workup

  1. extractionthe product was extracted with ethyl acetate (200 mL)
  2. customThe organic phase was separated
  3. washwashed with water (100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated in vacuo
  6. washthe crude material was washed with ether

Sources & evidence

ORD record
ord-aaebe78f869244c8af9ca0c2311dc668
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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