Hydrochloric Acid → Methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate

HRID 2218941Notes

Reaction equation

HRID 2218941 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH3:6][O:7][C:8](=[O:22])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[S:18](Cl)(=[O:20])=[O:19].Cl>ClCCl>[C:1]([NH:5][S:18]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]=1[C:8]([O:7][CH3:6])=[O:22])(=[O:19])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 22024122Methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 1.4 ml (13.3 mmol) of tert-butylamine are added dropwise to a solution of 1.00 g (3.58 mmol) of methyl-2-(chlorosulfonyl)-6-nitrobenzoate in 8 ml of dichloromethane, and the reaction mixture is then allowed to warm to room temperature. After 2 h, the reaction mixture is poured into ice-water, adjusted to pH 3 using 2 N aqueous hydrochloric acid and extracted with dichloromethane. The organic phase is then dried over sodium sulfate, filtered off and concentrated to dryness under reduced pressure. The residue that remains is digested with diethyl ether and filtered off with suction. This gives 1.06 g (91% of theory) of methyl 2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate of m.p. 89-91° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is then dried over sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated to dryness under reduced pressure
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-1fe0f291362846499c81fb6aeb309892
Source dataset
uspto-grants-2008_08
Patent number
US07414011B2

Reaction notes

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