3,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid → 4-Methoxybenzoic acid 6-[(2'-hydroxyethoxy-3,3''-dichloro-[1,1';3',1'']terphenyl-5'-carbonyl)-amino]-hexyl ester

HRID 324110Notes

Reaction equation

HRID 324110 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:16]=2[O:17][CH2:18][CH2:19][OH:20])[C:11](O)=[O:12])[CH:5]=[CH:6][CH:7]=1.[CH3:28][O:29][C:30]1[CH:45]=[CH:44][C:33]([C:34]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])=[O:35])=[CH:32][CH:31]=1>>[OH:20][CH2:19][CH2:18][O:17][C:16]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:9][C:10]([C:11]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][O:36][C:34](=[O:35])[C:33]2[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:45][CH:44]=2)=[O:12])=[CH:14][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1

Participants

3

Reactant 2

HCID 222373953,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acidHCID 572173864-Methoxybenzoic acid, 6-aminohexyl ester

Product 1

HCID 865836684-Methoxybenzoic acid 6-[(2'-hydroxyethoxy-3,3''-dichloro-[1,1';3',1'']terphenyl-5'-carbonyl)-amino]-hexyl ester

Procedure

The product was prepared as a colorless, viscous oil (0.675 g, 71%) from 3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid (0.605 g, 1.5 mmol) and 4-methoxybenzoic acid, 6-aminohexyl ester (0.565 g, 2.25 mmol) using a procedure similar to step 3 of example 164; 1H NMR (400 MHz, DMSO-d6) 1.33-1.46 (m, 4H), 1.50-1.58 (m. 2H),1.65-1.73 (m, 2H), 3.10-3.15 (m, 2H), 3.22-3.30 (m, 4H), 3.80 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 4.44 (t, J=6.6 Hz, 1H), 6.99-7.03 (m, 2H), 7.45-7.52 (m, 4H), 7.57-7.61 (m, 2H), 7.69 (s, 2H), 7.85-7.91 (m, 4H), 8.56 (t, J=5.5 Hz, 1H); IR (film) 3350, 2940, 1710, 1640, 1605, 1540, 1510, 1275 cm−1; mass spectrum[(+)ESI], m/z 636 (M+H)+.

Sources & evidence

ORD record
ord-6d80b4d31b46446f9aa3078c9d96ecca
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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