Acetic Acid → HCID 10287249, compound

HRID 393827Notes

Reaction equation

HRID 393827 reaction equation
[C:1]1([S:7]([NH:10][NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.CCOC(C)=O>[C:1]1([S:7]([NH:10][NH:11][C:12](=[O:20])[C:13]2[CH:14]=[CH:15][C:16]([NH:19][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 247403HCID 247403, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10287249HCID 10287249, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4Aminobenzoic acid 2-(phenylsulfonyl)hydrazide (100 mg, 0.34 mmol) was dissolved in THF (3.4 mL), treated with acetic acid (20 μL, 0.34 mmol) and benzaldehyde (23 μL, 0.34 mmol), and stirred for 5 minutes. Sodium triacetoxyborohydride (87 mg, 0.41 mmol) was added, and the reaction was stirred overnight. The reaction was diluted with EtOAc (100 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 3:2 hexanes/EtOAc to give 23 mg (18%) of the desired product. MS: 382.0 (M+1 for C20H19N3O3S1); mp 214-215° C.; TLC (SiO2) Rf=0.43 (1:1 hexane/EtOAc); HPLC (C18 column, 1:1 CH3CN/H2O+0.1% TFA) 99.04%, RT=8.309 min. HRMS (calc) 382.1225 (found) 382.1222; IR (KBr, cm−1): 3404, 3355, 3107, 1657, 1607, 1159. 1H NMR (DMSO-d6) δ 4.25 (d, 2H, J=5.6 Hz), 6.47 (d, 2H, J=8.3 Hz), 6.86-6.88 (m, 1H), 7.26-7.28 (m, 4H), 7.37-7.40 (m, 2H), 7.42-7.45 (m, 2H), 7.52-7.56 (m, 1H), 7.74 (d, 2H, J=7.8 Hz), 9.58 (s, 1H) 9.68 (s, 1H, 10.13 (s, 1H).

Workup

  1. stirringthe reaction was stirred overnight
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 3:2 hexanes/EtOAc

Sources & evidence

ORD record
ord-f3ea2a638ef34b9f9cc76768e28f376c
Source dataset
uspto-grants-2004_10
Patent number
US06809119B2

Reaction notes

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