Dichloromethane → HCID 18675327, compound

HRID 1635046Notes

Reaction equation

HRID 1635046 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([CH:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:7]=1.[Cu][C:22]#[N:23].C(Cl)Cl.[OH-].[NH4+]>CN(C=O)C>[CH3:20][O:19][C:5]1[CH:4]=[CH:3][C:2]([C:22]#[N:23])=[CH:7][C:6]=1[CH:8]1[C:13](=[O:14])[NH:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[O:9]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 18675130HCID 18675130, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18675327HCID 18675327, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-(5-bromo-2-methoxyphenyl)-2H-1,4-benzoxazin-3(4H)-one (I11) (0.90 g, 2.70 mmoles) in DMF (10 mL) was added copper (I) cyanide (1.3 g, 5 equiv.) and the mixture heated at 160° C. for 12 hours. The mixture was cooled and methylene chloride (100 mL) and aqueous ammonium hydroxide (10 mL) were added. The methylene chloride layer was separated and dried over MgSO4 which afforded the required product (I12) (0.67 g, 89%) upon evaporation in vacuo.

Workup

  1. temperatureThe mixture was cooled
  2. customThe methylene chloride layer was separated
  3. dry with materialdried over MgSO4 which

Sources & evidence

ORD record
ord-41e8a45205d4445397fd2bcea596efc3
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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