Acetic Acid → HCID 53726079, compound

HRID 2121630Notes

Reaction equation

HRID 2121630 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:17]([NH:21][NH2:22])([O:19][CH3:20])=[O:18].CC(O)=O>C(O)C.O>[C:17]([NH:21][N:22]=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 80519Methyl carbazateHCID 38568024-(4-Fluorophenoxy)benzaldehyde

Product 1

HCID 53726079HCID 53726079, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-(4-fluorophenoxy)benzaldehyde (277 mg, 1.28 mmol) in ethanol (10 mL) was added a solution of carbomethoxyhydrazine (180 mg, 2.0 mmol) in water (5 mL), followed by AcOH (0.1 mL) at room temperature. The mixture was stirred at room temperature for 17 h and water (20 mL) was added. The resulting solid was collected by filtration, washed with water and dried in vacuo to yield the title compound as a white solid (228 mg, 0.74 mmol, 58%), mp: 109-111° C. 1H NMR (DMSO-d6): δ 11.05 (s, 1H), 8.00 (s, 1H), 7.64 (d, J=8.7, 2H), 7.30-6.99 (m, 6H), 3.69 (s, 3H).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-74febeafd3f943c58ac9e57f2a13b5f5
Source dataset
uspto-grants-2004_02
Patent number
US06696442B2

Reaction notes

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