Formaldehyde → HCID 478201, compound

HRID 1005565Notes

Reaction equation

HRID 1005565 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:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH2:45]=O>C(OCC)(=O)C>[CH2:38]([N:37]([CH2:45][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)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1783CapravirineHCID 7656Dibenzylamine

Product 1

HCID 478201HCID 478201, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound 111 (306 mg, 0.7 mmol), dibenzylamine (138 mg, 0.7 mmol) and paraformaldehyde (22.0 mg., 0.733 mmol) in ethyl acetate (4 mL) was heated under reflux in an atmosphere of nitrogen for 8 hours. After cooling down at room temperature, the reaction mixture was purified by chromatography on a silica gel column (eluate: ethyl acetate) to give the compound 114 (295 mg, 64%). Rf 0.70 (EtOAc). 1H-NMR (CDCl3): δH1.31 (6 H, d, J 6.6 Hz, (CH3)2CH), 3.18 (1 H, sep, J 6.6 Hz, (CH3)2CH), 3.57 (4H, s, 2 x benzyl-CH2), 4.04 (2 H, d, J 6.0 Hz, NCH2NH), 4.88 (1H, t, 6.0 Hz, NCH2NH), 5.19 (2 H, s, CH2O), 5.24 (2 H, s, NCH2), 6.68 (2 H, d, J 1.5 Hz, arom 2- and 6-H), 6.78 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.03 (1 H, t, J 1.5 Hz, arom 4-H), 7.20-7.35 (10 H, m, 2 x benzyl), 8.43 (2 H, d-like, 4-pyridyl 3- and 5-H). Elementary analysis (for C35H35N5O2SCl2) Calcd.: C, 63.63% H, 5.34% N, 10.60% S, 4.85% Cl, 10.73% Found: C, 63.39% H, 5.44% N, 10.63% S, 4.88% Cl, 10.53% The above compounds are shown as follows. ##STR6##

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 8 hours
  3. customthe reaction mixture was purified by chromatography on a silica gel column (eluate: ethyl acetate)

Sources & evidence

ORD record
ord-8344039ac75e4ecdaf347fc9e45b0bfb
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

Loading…