Chloroacetic Acid → HCID 57038976, compound

HRID 2082695Notes

Reaction equation

HRID 2082695 reaction equation
Cl[CH2:2][C:3]([Cl:5])=O.[NH2:6][N:7]1[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])([OH:17])[C:15]2[C:10](=[CH:11][CH:12]=C(Cl)C=2)[N:9]=[CH:8]1.[Cl:26][CH2:27][C:28](O)=O>C1C=CC=CC=1>[Cl:26][CH2:27][C:28]1[N:9]([C:10]2[CH:11]=[CH:12][C:3]([Cl:5])=[CH:2][C:15]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[O:17])[CH:8]=[N:7][N:6]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 6577Chloroacetyl chlorideHCID 20360436HCID 20360436, compound

Product 1

HCID 57038976HCID 57038976, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Amino-5,2'-dichlorobenzophenone is reacted with formic acid, whereby 5, 2'-dichloro-2-formylaminobenzophenone (pale yellow granules melting at 106° to 107° C) is obtained. The product is then reacted with hydrazine hydrate, whereby 3-amino-6-chloro-4-(2-chlorophenyl)-3,4-dihydro-4-hydroxyquinazoline (colorless granules melting at 198° C (effervescence)) is obtained. The product is reacted with chloroacetyl chloride, whereby a bis-(monochloroacetyl) derivative of 3-amino-6-chloro-4-(2-chlorophenyl)-3,4-dihydro-4-hydroxyquinazoline (colorless powdery crystals melting at 157° to 158° C) is obtained. Further, the product is treated with monochloroacetic acid in dry benzene under refluxing, whereby crystals of 2-(3-chloromethyl-s-triazol-4-yl)-5, 2'-dichlorobenzophenone are obtained. Recrystallization from chloroform-n-hexane gives colorless granules melting at 139° to 140° C. Overall yield: 34%.

Workup

  1. customis obtained
  2. temperatureunder refluxing

Sources & evidence

ORD record
ord-6d4a068daa8a4a69afcae1d9df55b5cb
Source dataset
uspto-grants-1978_04
Patent number
US04082764

Reaction notes

Loading…