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Water → 4-(2,4-Dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-benzonitrile

HRID 1663088
Notes
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Reaction equation

HRID 1663088 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)#[N:14].N12CCCN=C1CCCCC2.O>CN(C=O)C>[O:12]=[C:5]1[N:6]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=2[C:2](=[O:3])[O:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8359Isatoic AnhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 589898174-(2,4-Dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-benzonitrileYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a stirred mixture of isatoic anhydride (2.0 g) and 4-cyano-benzyl bromide (2.40 g) in DMF (20 ml) was added drop-wise 1,8-diazabicyclo[5,4,0]-undec-7-ene (2.20 ml). The reaction mixture was stirred at room temperature for 22 hours, cooled in an ice-bath and water (75 ml) was added. The resulting precipitated material was isolated by filtration and re-crystallised from hot toluene and gave the title compound (1.65 g) as an off-white solid. 13C-NMR (DMSO-d6) δ 158.7, 148.2, 141.2, 141.1, 136.9, 132.4, 129.5, 128.8, 128.1, 127.5, 123.7, 118.6, 114.8, 112.2, 110.2, 47.3.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe resulting precipitated material
  3. customwas isolated by filtration
  4. customre-crystallised from hot toluene

Sources & evidence

ORD record
ord-2e5a77bb6506444988184e3a32a8036f
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08034811B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes