Pyridine → HCID 19106814, compound

HRID 1197453Notes

Reaction equation

HRID 1197453 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[C:16]([OH:23])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13]2)=[O:10])=[CH:4][CH:3]=1.C(Cl)(=[O:26])C.N1C=CC=CC=1>ClCCl>[C:21]([OH:22])(=[O:26])[CH3:20].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[C:16]([OH:23])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18961882HCID 18961882, compound

Product 1

HCID 19106814HCID 19106814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(p-chlorophenyl)-3-(3,4-dihydro-8-hydroxy-4-oxo-3-quinazolinyl)urea (0.66 g, 2.00 mmol) in dichloromethane is treated with acetyl chloride (0.155 mL, 2.11 mmol) and pyridine (0.165 mL, 2.04 mmol), stirred overnight, washed sequentially with 5% hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous MgSO4 and concentrated in vacuo to obtain a solid. The solid is washed with dichloromethane and dried to give the title product as a white solid, 0.30 g, mp 216°-218° C., which is identified by 1HNMR spectral analysis.

Workup

  1. washwashed sequentially with 5% hydrochloric acid, saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customto obtain a solid
  5. washThe solid is washed with dichloromethane
  6. customdried

Sources & evidence

ORD record
ord-687af377f3c946b9967a2584eed3a046
Source dataset
uspto-grants-1994_01
Patent number
US05276038

Reaction notes

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