Pivalic acid → HCID 18957771, compound

HRID 2379352Notes

Reaction equation

HRID 2379352 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](O)=[O:4].[N+:8]([C:11]1[CH:12]=[C:13]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]([CH3:7])([C:3]([NH:20][S:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)(=[O:19])=[O:18])=[O:4])[CH3:6]

Participants

6

Reactant 3

HCID 6417Pivalic acidHCID 67138Benzenesulfonamide, 3-nitro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18957771HCID 18957771, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of trimethylacetic acid (5.55 g, 54 mmol), 3-nitrobenzenesulphonamide (11 g, 54 mmol) and 4-dimethylaminopyridine (6.65 g, 54 mmol) in anhydrous dichloromethane (400 ml), under an atmosphere of nitrogen, was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (10.43 g, 54 mmol). The mixture was stirred at ambient temperature for 24 h. The mixture was extracted with 1M NaOH (50 ml) and the separated aqueous phase was mixed with dichloromethane (200 ml) and acidified with 5M HCl. The two layers were separated and the aqueous phase was further extracted with dichloromethane (2×100 ml). The combined organic phases were dried (Na2SO4) and evaporated to dryness. The resultant solid was recrystallised from methanol to afford the title compound (9 g, 58%) as a colourless solid. mp 178°-81° C. 1H NMR (360 MHz, D6-DMSO) δ 1.07 (9H, s), 7.95 (1H, t, J=8.0 Hz), 8.30-8.34 (1H, m), 8.52-8.56 (1H, m), 8.57-8.60 (1H, m), 12.02 (1H, brs).

Workup

  1. extractionThe mixture was extracted with 1M NaOH (50 ml)
  2. additionthe separated aqueous phase was mixed with dichloromethane (200 ml)
  3. customThe two layers were separated
  4. extractionthe aqueous phase was further extracted with dichloromethane (2×100 ml)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customevaporated to dryness
  7. customThe resultant solid was recrystallised from methanol

Sources & evidence

ORD record
ord-64efe0b30afb458abdf0f49f6b4c2136
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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