Thionyl Chloride → HCID 68023578, compound
Reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([OH:19])=O)=[CH:11]2)([O-:7])=[O:6].[Cl-].[Cl-].[Ca+2].C([O-])(O)=O.[Na+].[CH3:28][O:29][CH:30]([O:33][CH3:34])[CH2:31][NH2:32]>O1CCOCC1.O1CCOCC1.O>[CH3:28][O:29][CH:30]([O:33][CH3:34])[CH2:31][NH:32][C:17]([C:12]1[NH:13][C:14]2[C:10]([CH:11]=1)=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=2)=[O:19]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Thionyl chloride (8 ml, 110 mmol, 5 eq.) was added to a suspension of the compound of formula (III) (4.53 g, 22 mmol, 1 eq.) in dry dioxane (50 ml). The final suspension was refluxed in dry atmosphere (CaCl2 valve) for 2 h, and the reaction turned to a light brown solution while proceeding. The reaction was cooled to 25° C. and organic volatiles were removed under reduced pressure, then dry toluene (25 ml) was added and removed under vacuum, this operation was repeated twice. The brown residue (22 mmol, 1 eq.) was added portion wise to a cooled solution at 0° C. of NaHCO3 (3.7 g, 43.95 mmol, 2 eq.) and 2,2-dimethoxy-ethylamine (2.39 ml, 21.97 mmol, 1 eq.) in dioxane/water 4:1 (100 ml), the suspension was stirred for 2 hours at rt. Organic volatiles were removed under reduced pressure and the yellow precipitate was filtered and dried to give 5-nitro-1H-indole-2-carboxylic acid (2,2-dimethoxy-ethyl)-amide (IV). Yield=5.80 g (90%).
Workup
- customorganic volatiles were removed under reduced pressure
- additiondry toluene (25 ml) was added
- customremoved under vacuum
- customOrganic volatiles were removed under reduced pressure
- filtrationthe yellow precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-ef8a1f33cdc24a2cad7430cb2c7cf1eb
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207165B2
Reaction notes
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