Citric Acid → HCID 13670774, compound

HRID 963071Notes

Reaction equation

[C:1]([C:4]1[S:13][C:12]2[N:11]3[C:14]([CH3:17])=[N:15][N:16]=[C:10]3[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:6]=2[CH:5]=1)(=[O:3])C.Cl[O-].[Na+].S([O-])(O)=[O:29].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[C:6]2[CH:5]=[C:4]([C:1]([OH:29])=[O:3])[S:13][C:12]=2[N:11]2[C:14]([CH3:17])=[N:15][N:16]=[C:10]2[CH2:9][N:8]=1

Participants

Reactant 4

HCID 311Citric Acid

HCID 12434328HCID 12434328, compound

HCID 23665760Sodium Hypochlorite

HCID 23665763Sodium Bisulfite

Product 1

HCID 13670774HCID 13670774, compoundYield 49.7%

Conditions

Temperature: 60 °C

Procedure

2-Acetyl-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (1.0 g) synthesized by the method described in Artneim.-Forsch./Drug Res. 28 (II), Heft 7, 1153-1158 (1978) was added to a 10% aqueous sodium hypochlorite solution (21 ml), and the mixture was stirred at 60° C. for 1.5 hours. Sodium hydrogensulfite (2.9 g) was added to the reaction mixture. Then, an aqueous citric acid solution was added to adjust the reaction mixture to pH 3. The obtained crystals were collected by filtration, and washed with water to give 0.5 g of (4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-2-yl)carboxylic acid.

Workup

filtrationThe obtained crystals were collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-9aa8df54cf804bc88edba53e3784374a
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760032

Reaction notes

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