Dimethylformamide → [1,1'-Biphenyl]-4-carboxylic acid, 2-(phenylsulfonyl)hydrazide

HRID 393830Notes

Reaction equation

HRID 393830 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][NH2:10])=[O:8])=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN(C=O)C>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:26]1([S:32]([NH:10][NH:9][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:2][CH:3]=2)=[O:8])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7369Benzenesulfonyl chlorideHCID 72718p-PhenylbenzhydrazideHCID 81531Diisopropylethylamine

Product 1

HCID 3386671[1,1'-Biphenyl]-4-carboxylic acid, 2-(phenylsulfonyl)hydrazide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Biphenyl-4-carboxylic acid hydrazide (0.5 g, 2.36 mmol) was suspended in THF (26 mL). N,N-diisopropylethylamine (1.64 mL, 9.44 mmol) was added, and the reaction was cooled to 0° C. Phenylsulfonyl chloride (0.33 mL, 2.59 mmol) was added followed by DMAP (5 mg, 0.04 mmol). The reaction was allowed to warm to room temperature. The solution was orange after it stirred for 1 hour; DMF (5 mL) was added, and the solution became clear. After 3 hours of stirring, the solution was diluted with EtOAc (150 mL). It was then washed with saturated sodium bicarbonate and brine and dried over Na2SO4. The reaction was then concentrated down and triturated with CH2Cl2. The desired product was isolated (0.19 g, 22.7%). MS: 351.1 (M)−1 for C19H16N2O3S); mp 216-219° C. TLC: SiO2, Rf=0.55 (1:1 hexane/EtOAc). Analysis C19H16N2O3S.0.25 H2O: (calc) C, 63.94; H, 4.66; N, 7.85. (found) C, 63.76; H, 4.64; N, 7.76. HPLC: (30% H2O/70% CH3CN/0.1% TFA), RT=3.731 min. Purity: 94.16%. IR (KBr, cm−1) 3337, 3035, 2811, 1655, 1340, 1156. 1H NMR (400 MHz, DMSO) δ 7.26-8.00 (m, 14H), 10.01 (s, 1H, 10.71 (s, 1H).

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter 3 hours of stirring
  3. washIt was then washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe reaction was then concentrated down
  6. customtriturated with CH2Cl2

Sources & evidence

ORD record
ord-29629f71b44940b4b3f3aec2ca3322fd
Source dataset
uspto-grants-2004_10
Patent number
US06809119B2

Reaction notes

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