Chloroacetyl chloride → HCID 21325746, compound

HRID 25948Notes

Reaction equation

HRID 25948 reaction equation
CN(C)P(=[O:10])(N(C)C)N(C)C.[Cl:12][CH2:13][C:14](Cl)=[O:15].O.O.Br.Br.[NH2:21][CH2:22][C:23]1[N:32]([NH:33][C:34](=[O:36])[CH3:35])[C:31](Br)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Cl:45])[CH:29]=2)[N:24]=1>CCOCC>[Cl:12][CH2:13][C:14]([NH:21][CH2:22][C:23]1[N:32]([NH:33][C:34](=[O:36])[CH3:35])[C:31]([OH:10])([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Cl:45])[CH:29]=2)[N:24]=1)=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 12679HexamethylphosphoramideHCID 21325728HCID 21325728, compound

Product 1

HCID 21325746HCID 21325746, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of hexamethylphosphoric triamide (12 ml) and chloroacetyl chloride (0.452 g), 2-aminomethyl-3-acetamido-4-bromo-4-(2-chlorophenyl)-6-chloro-3,4-dihydroquinazoline dihydrobromide dihydrate (1.276 g) is added, and the resultant mixture is stirred at room temperature for 5 hours. The reaction mixture is mixed with ether and washed with aqueous sodium bicarbonate and water in order. The precipitate is dried to give 2-(2-chloroacetamidomethyl)-3-acetamido-4-hydroxy-4-(2-chlorophenyl)-6-chloro-3,4-dihydroquinazoline (0.63 g). This product (0.6 g) is dissolved in acetic acid (6 ml) to give a solution, which is refluxed for 2 hours. The reaction mixture is evaporated under reduced pressure. The residue is extracted with ethyl acetate. The organic layer is washed with aqueous sodium bicarbonate and water in order, dried and evaporated to remove the ethyl acetate. The residue is chromatographed on a column of silica gel, which is eluted with methanol to give 2',5-dichloro-2-[3-(2-chloroacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4 -yl]-benzophenone (0.15 g).

Workup

  1. additionis added
  2. washwashed with aqueous sodium bicarbonate and water in order
  3. customThe precipitate is dried

Sources & evidence

ORD record
ord-2f5ea647698d4f9d8b658de3681ee9f6
Source dataset
uspto-grants-1979_04
Patent number
US04147700

Reaction notes

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