HCID 444235, compound → HCID 178455663, compound

HRID 1170216Notes

Reaction equation

HRID 1170216 reaction equation
[CH3:1][CH:2]([S:5]([O:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:7])=[O:6])[CH2:3][CH3:4].[CH3:13][N+:14]1[CH:18]=[CH:17][NH:16][CH:15]=1>>[CH3:1][CH:2]([S:5]([O-:8])(=[O:7])=[O:6])[CH2:3][CH3:4].[CH2:9]([N+:16]1[CH:17]=[CH:18][N:14]([CH3:13])[CH:15]=1)[CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 444235HCID 444235, compoundHCID 86618675HCID 86618675, compound

Product 1

HCID 178455663HCID 178455663, compoundYield 80%

Procedure

Butyl 2-butanesulfonate (24.88 g; 154 mmol) was mixed with 1-methyl imidazolium (12.30 g; 150 mmol) and the reaction mixture was allowed to stand at room temperature (25° C.) for 60 hours. After this period of time, the yellow reaction mixture became solidified. The crystalline mass was crushed, washed two times with ethyl acetate and dried under vacuum, which produced colorless crystals of 1-butyl-3-methyl imidazolium 2-butanesulfonate (33.10 g, 80% yield), melting point 76.1° C. RMN—1H (CDCl3) δ: 9.80 (1H, s, C—H imidazolium); 7.53 (1H, t, J=1.5 Hz, C—H imidazolium); 7.39 (1H, t, J=1.5 Hz, C—H imidazolium); 4.15 (2H, t, J=7.5 Hz, NCH2); 3.92 (3H, s, NCH3); 2.72-2.60 (1H, m, CH3CH2CH(CH3)SO3); 2.20 5-2.05 (1H, m, CH3CH2CH(CH3)SO3); 1.87 (2H, quintet, J=7.5 Hz, CH2); 1.54-1.30 (3H, m, CH3CH2CH(CH3)SO3 and CH2); 1.32 (3H, d, J=6.8 Hz, CH3CH2CH(CH3)SO3); 0.99 (3H, t, J=7.5 Hz, CH3CH2CH(CH3)SO3); 0.94 (3H, t, J−7.5 Hz, CH3). RMN—13C (CDCl3) δ: 137.6; 123.6 and 121.8 (C—H imidazolium); 56.7 (CH3CH2CH(CH3)SO3); 49.2 (NCH2); 36.0 (NCH3); 31.8; 24.6 and 19.0 (CH2); 14.5; 13.1 and 11.5 (CH3).

Workup

  1. customto stand at room temperature
  2. custom(25° C.)
  3. customfor 60 hours
  4. waitAfter this period of time
  5. customThe crystalline mass was crushed
  6. washwashed two times with ethyl acetate
  7. customdried under vacuum, which

Sources & evidence

ORD record
ord-d32e90588bbb4d43af43c77a29f37b20
Source dataset
uspto-grants-2010_11
Patent number
US07825259B2

Reaction notes

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