Water → HCID 66651303, compound

HRID 419766Notes

Reaction equation

HRID 419766 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[C:12](=[C:14]([C:18]#[N:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.[OH2:20]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]3[C:12](=[C:14]([C:18]([NH2:19])=[O:20])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 962WaterHCID 66651598HCID 66651598, compound

Product 1

HCID 66651303HCID 66651303, compound

Procedure

A mixture of EXAMPLE 1D (0.8 g) in polyphosphoric acid (8 mL) was stirred at 100° C. for 3 hours. The mixture was cooled, treated with water and extracted with dichloromethane. The solid that precipitated out of the organic layer was filtered, washed with water and dried to afford the title compound. 1H NMR (DMSO-d6) δ 9.24 (s, 1H), 8.33 (d, J=7.9 Hz, 1H), 8.18-8.21 (m, 1H), 8.11-8.14 (m, 2H), 7.94 (s, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.15-7.19 (m, 2H), 3.89 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane
  3. customThe solid that precipitated out of the organic layer
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-de4b6bbc125340208ade085bd1215a62
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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