Sodium Carbonate → HCID 67162631, compound

HRID 42344Notes

Reaction equation

HRID 42344 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[CH:5][C:4]=1C.BrC1C=CC(S(Cl)(=O)=O)=C([C:29]([F:32])([F:31])[F:30])C=1.C([O-])([O-])=O.[Na+].[Na+]>[C-]#N.[C-]#N.[Zn+2].CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])(=[O:10])=[O:11])=[C:7]([C:29]([F:32])([F:31])[F:30])[CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27786084-Bromo-2-(trifluoromethyl)benzenesulfonyl chlorideHCID 582753444-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide

Product 1

HCID 67162631HCID 67162631, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178476572HCID 178476572, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

4-Aminomethyl-N-tert-butyl-2-trifluoromethyl-benzenesulfonamide was synthesized in a manner analogous to 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide in Example 4, using 4-bromo-2-(trifluoromethyl)benzene-1-sulfonyl chloride in place of 4-bromo-3-methylbenzene-1-sulfonyl chloride. In the second step, K4-[Fe(CN)6].3H2O was used in place of Zn(CN)2, Pd(OAc)2/dppf was used as the catalyst, Na2CO3 was used as base and the reaction mixture was stirred at 110° C. with microwave irradiation for one hour.

Sources & evidence

ORD record
ord-57362e0c918042e0b418f4e8e28291a4
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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