Hydrochloric Acid → 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-dodecylthiophene-2-sulfonamide

HRID 735835Notes

Reaction equation

HRID 735835 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:17][C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C.[CH2:31]([NH2:43])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].Cl>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:17][C:16]([S:18]([NH:43][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:20])=[O:19])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13583DodecylamineHCID 81531DiisopropylethylamineHCID 178101595-[(1,3-Dioxoisoindol-2-yl)methyl]thiophene-2-sulfonyl chloride

Product 1

HCID 671880585-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-dodecylthiophene-2-sulfonamideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]thiophene-2-sulfonyl chloride (2.00 g, 5.85 mmol), DIEA (1.134 g, 8.78 mmol) in DCM (20 mL) was added dodecyl amine (1.41 g, 7.61 mmol) at rt and the reaction mixture was stirred for 2 h at rt. A 1 M aqueous solution of HCl (10 mL) was added and the aqueous layers were extracted with DCM (2×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford a yellowish oil. This crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 1/4 to 4/1 in about 0.5 h) to give the title compound as a white solid (2.10 g, 73%). 1H NMR (CD3OD, 300 MHz) δ 7.91 (m, 2H), 7.85 (m, 2H), 7.43 (d, 1H, J=3.7 Hz), 7.17 (d, 1H, J=3.7 Hz), 5.05 (s, 2H), 2.90 (t, 2H, J=6.9 Hz), 1.50-1.38 (m, 2H), 1.35-1.16 (m, 18H), 0.86 (t, J=7.9 Hz, 3H) M−(LC/MS): 489.3; M+(LC/MS): 491.2. HPLC (Condition A), Rt: 6.64 min (HPLC purity: 95.9%).

Workup

  1. extractionthe aqueous layers were extracted with DCM (2×30 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a yellowish oil
  6. customThis crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 1/4 to 4/1 in about 0.5 h)

Sources & evidence

ORD record
ord-4a2b8e32f3b64b438fd6b4ff66838748
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

Loading…