Formaldehyde → HCID 478199, compound

HRID 1005563Notes

Reaction equation

HRID 1005563 reaction equation
[C:1](=[O:29])([O:3][CH2:4][C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[C:7]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)[NH2:2].[CH2:30]([NH:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].[CH2:39]=O>C(OCC)(=O)C>[CH2:30]([N:34]([CH2:39][NH:2][C:1](=[O:29])[O:3][CH2:4][C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[C:7]([S:13][C:14]2[CH:15]=[C:16]([Cl:21])[CH:17]=[C:18]([Cl:20])[CH:19]=2)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1783CapravirineHCID 8148Dibutylamine

Product 1

HCID 478199HCID 478199, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the above prepared 5-(3,5-dichlorophenylthio)-4-isopropyl-1-(4-pyridylmethyl)-1H-imidazol-2-ylmethyl carbamate (111) (219 mg, 0.5 mmol), di-n-butylamine (85 mg, 0.5 mmol) and paraformaldehyde (17.5 mg, 0.583 mmol) in ethyl acetate (3mL) was heated under reflux in an atmosphere of nitrogen for 5 days. After cooling down at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in a small amount of ether, and hexane was added thereto. The precipitated insoluble material was filtered off, and the filtrate was cooled at -50° C. The purified precipitate was collected to give the compound 112 (167 mg, 66%) as oil. 1H-NMR (CDCl3): δH 0.88 (6H, t, J 6.9 Hz, 2 x CH3), 1.31 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.20-1.42 (8 H, m, 2 x --CH2 --), 2.34 (4 H, t, J 7.8 Hz, 2 x --CH2 --), 3.17 (1 H, sep, J 6.9 Hz, (CH3)2CH), 4.06 (2 H, d, J 6.0 Hz, NCH2NH), 4.82 (1 H, t, J 6.0 Hz, NCH2NH), 5.18 (2 H, s, CH2O), 5.24 (2 H, 8, NCH2), 6.68 (2 H, d, J 1.5 Hz, arom 2- and 6-H), 6.79 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.03 (1 H, t, J 1.5 Hz, arom 4-H), 8.42 (2 H, d-like, 4-pyridyl 3- and 5-H). Elementary analysis (C29H39N5O2SCl2) Calcd. : C, 58.78% H, 6.63% N, 11.82% S, 5.41% Cl, 11.96% Found: C, 58.72% H, 6.76% N, 11.63% S, 5.59% Cl, 11.63% hydrochloride of 112 Elementary analysis (for C29H39N6O2SCl5 3HCl 1.5H2O) Calcd. : C, 47.78% H, 6.22. N, 9.61% S, 4.40% Cl, 24.31% Found: C, 47.95% H, 6.01% N, 9.77% S, 4.63% Cl, 23.93%

Workup

  1. additionA suspension of the
  2. temperaturewas heated
  3. temperatureunder reflux in an atmosphere of nitrogen for 5 days
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in a small amount of ether, and hexane
  6. additionwas added
  7. filtrationThe precipitated insoluble material was filtered off
  8. temperaturethe filtrate was cooled at -50° C
  9. customThe purified precipitate was collected

Sources & evidence

ORD record
ord-7db2aa037c754e6792b3292e329ba60b
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

Loading…