Water → 6-Chloroquinazolin-2-amine

HRID 1850301Notes

Reaction equation

HRID 1850301 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.C(=O)(O)O.[NH2:15][C:16]([NH2:18])=[NH:17].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:17]=[C:16]([NH2:18])[N:15]=[CH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 27735865-Chloro-2-fluorobenzaldehyde

Product 1

HCID 211839426-Chloroquinazolin-2-amineYield 50%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 5-chloro-2-fluoro-benzaldehyde (109) (5 g, 31.6 mmol) and guanidine carbonate (7.5 g, 41.1 mmol) was heated at 140° C. in DMA (50 mL) for 3 h. 100 ml water was added and after refrigeration, a solid was isolated by filtration, and dried under vacuum to give the product (110) (2.8 g, 15.8 mmol, 50% yield). ESI-MS (M+1): 180 calc. for C8H6ClN3 179.

Workup

  1. customafter refrigeration, a solid was isolated by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a1b53042b04f414eb498958013397fb8
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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