Hydrochloric Acid → HCID 71667659, compound

HRID 928945Notes

Reaction equation

HRID 928945 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9]S[C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][O:17]C=C)=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28].Cl.[OH:30]S(O)(=O)=O.FC(F)(F)C(O)=O.S1(CCCC1)(=O)=O>ClCCCl.ClCCl.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C.CS(C)=O.CCOCC>[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:30][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28]

Participants

12

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 31347SulfolaneHCID 89704860HCID 89704860, compound

Product 1

HCID 71667659HCID 71667659, compound

Reagents, catalysts & solvents 6

HCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 12679HexamethylphosphoramideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

4-Fluoro-5-((2-fluoro-4-iodophenyl)amino)-N-(2-(vinyloxy)ethoxy)benzo[d]thiazole-6-carboxamide can be reacted in the presence of acid (such as HCl, H2SO4, trifluoroacetic acid) in appropriate solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer dichloromethane and 1,2-dichloroethane) for some time (1-12 h, prefer 3-10 h). 4-Fluoro-5-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxy ethoxy)benzo[d]oxazole-6-carboxamide is obtained after conventional workup.

Sources & evidence

ORD record
ord-a3ea59415a1f4ca29ce207eaaf88832f
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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