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Oxalyl chloride → HCID 22394525, compound

HRID 991551
Notes
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Reaction equation

HRID 991551 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]=[C:12]([C:21]4[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=4)[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)(=O)C([Cl:33])=O>ClCCl.CN(C)C=O>[ClH:33].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]=[C:12]([C:21]4[CH:29]=[CH:28][C:24]([C:25]([Cl:33])=[O:26])=[CH:23][CH:22]=4)[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:9][C:4]=2[O:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 99081314-[4-(2H-1,3-Benzodioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl]benzoic acid

Product 1

HCID 22394525HCID 22394525, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzoic acid (379 mg; 0.98 mmol) was suspended in dry dichloromethane (20 ml) under argon and treated sequentially with oxalyl chloride (0.1 ml) then N,N-dimethylformamide (1 drop). The mixture was stirred at ambient temperature for 1 h. More oxalyl chloride (2×0.1 ml) was added at 1 h and 2 h and the mixture stirred at ambient temperature for 5 h. Volatiles were removed under reduced pressure to give the title compound as an orange powder: m/z (methyl ester; API): 400.3 (M+H)+.

Workup

  1. stirringthe mixture stirred at ambient temperature for 5 h
  2. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-2ba57aa065c14a69be40267bd93f70c0
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06465493B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes