3-Nitrobenzaldehyde → HCID 9929475, compound

HRID 1386045Notes

Reaction equation

HRID 1386045 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[S:12]1(=[O:20])(=[O:19])[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1.[NH2:21][C:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH:23]=1>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]2[C:23]3[C:24](=[O:28])[CH2:25][CH2:26][CH2:27][C:22]=3[NH:21][C:14]3[CH2:15][CH2:16][CH2:17][S:12](=[O:20])(=[O:19])[C:13]2=3)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 788923-Aminocyclohex-2-en-1-oneHCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

Product 1

HCID 9929475HCID 9929475, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-nitrobenzaldehyde (151 mg, 1.00 mmol), tetrahydrothiopyran-3-one-1,1-dioxide (148 mg, 1.00 mmol), prepared according to the method described in J. Heterocycl. Chem. (1990), 27, 1453, and 3-amino-2-cyclohexen-1-one (111 mg, 1.00 mmol) in ethanol (7 mL) was heated at reflux for 24 hours and cooled. The solid that precipitated was washed with ethanol, dried, and triturated with hot methanol to provide the title compound. MS (APCI) m/e 375 (M+H)+; 1H NMR (DMSO-d6) 1.75 (m, 1H), 1.90 (m, 1H), 2.22 (m, 4H), 2.55 (m, 4H), 3.22 (m, 2H), 5.15 (s, 1H), 7.55 (t, 1H), 765 (d, 1H), 8.00 (m, 1H), 9.48 (br s, 1H); Anal. Calcd for C, 57.74; H, 4.85; N, 7.48. Found: C, 57.41; H, 4.75; N, 7.39.

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturecooled
  3. customThe solid that precipitated
  4. washwas washed with ethanol
  5. customdried
  6. customtriturated with hot methanol

Sources & evidence

ORD record
ord-ac138a6a6c6d405eafcf0a1c3e22729c
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

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