4-(Trifluoromethyl)benzaldehyde → HCID 25023665, compound

HRID 735836Notes

Reaction equation

HRID 735836 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][C:6]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:10])=[O:9])=[CH:5][CH:4]=1.[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:12]([NH:11][S:8]([C:6]1[S:7][C:3]([CH2:2][NH:1][CH2:30][C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=2)=[CH:4][CH:5]=1)(=[O:9])=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67186603HCID 67186603, compound

Product 1

HCID 25023665HCID 25023665, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-(aminomethyl)-N-dodecylthiophene-2-sulfonamide (797 mg, 2.21 mmol) and 4-trifluoromethyl-benzaldehyde (350 mg, 2.01 mmol) in DCE (50 mL) was added at once NaBH(OAc)3 (596 mg, 2.81 mmol) and the resulting mixture was stirred overnight at rt. 30 mL of a saturated aqueous solution of NaHCO3 were added to the reaction mixture, the aqueous layer was separated and washed with DCM (3×200 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 1/2 in about 1 h) to give the title compound as a colorless oil (675 mg, 64%). 1H NMR (CDCl3, 300 MHz) δ 7.60 (m, 2H), 7.46 (m, 2H), 7.37 (d, 0.7H, J=8.0 Hz), 6.88 (d, 1H, J=3.8 Hz), 4.00 (s, 2H), 3.90 (s, 2H), 3.02 (m, 2H), 1.85-1.55 (m, 2H), 1.5 (m, 2H), 1.22 (s, 18H), 0.87 (t, 3H, 6.6 Hz). M−(LC/MS (ESI)): 517.2; M+(LC/MS (ESI)): 519.2 HPLC (Condition A), Rt: 5.27 min (HPLC purity: 97.2%).

Workup

  1. customthe aqueous layer was separated
  2. washwashed with DCM (3×200 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a yellowish oil
  7. customThis crude product was purified by column chromatography over silica gel (AcOEt/c-Hex 1/4 to 1/2 in about 1 h)

Sources & evidence

ORD record
ord-7301e256ba474afb84001e88befe48e8
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

Loading…