Triethylamine → HCID 54188717, compound

HRID 274809Notes

Reaction equation

HRID 274809 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:3]([NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([CH2:43][C:44](Cl)=[O:45])=[CH:35]1>ClCCl.C(OCC)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11]([NH:10][CH:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:2]([NH:1][C:44](=[O:45])[CH2:43][C:36]2[C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[NH:34][CH:35]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122193831H-Indole-3-acetyl chlorideHCID 54496433HCID 54496433, compound

Product 1

HCID 54188717HCID 54188717, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [S-(R*,R*)] and [R-(R*,R*)]-N-(2-amino-1,2-diphenylethyl)-N'-(4-chlorophenyl)urea (0.1 g, 0.27 mmol) in dichloromethane (5 mL) is added triethyl amine (0.03 g, 0.27 mmol) followed by indole-3-acetic acid chloride (0.05 g, 0.27 mmol). The mixture is stirred 1.5 hours at room temperature before diluting with diethyl ether and washing with aqueous 2M HCl, aqueous 1M NaOH, saturated aqueous NaCl, and drying (MgSO4). Filtration and concentration gives an oil which is purified by flash chromatography (SiO2, EtOAc/hexane eluent) to provide 0.05 g (33%) of desired product, mp 224°-227° C. IR (KBr): 3360, 1549, 1492, 1226, 698 cm-1 ; NMR (DMSO-d6): 3.56 (s, 2H), 5.07 (m, 2H), 6.78-7.45 (m, 20H), 8.65 (m, 2H), 10.81 (s, 1H). Analysis calculated for C31H27ClN4O2.0.5H2O: C, 69.98; H, 5.30; N, 10.53. Found: C, 69.65; H, 5.41; N, 10.56.

Workup

  1. washwashing with aqueous 2M HCl, aqueous 1M NaOH, saturated aqueous NaCl
  2. dry with materialdrying (MgSO4)
  3. filtrationFiltration and concentration
  4. customgives an oil which
  5. customis purified by flash chromatography (SiO2, EtOAc/hexane eluent)

Sources & evidence

ORD record
ord-9f0ab8d635654a7b8deefd7c8c3d94ec
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

Loading…