Ethanol → HCID 178457599, compound

HRID 2121071Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[O:5][CH2:6][CH2:7][CH2:8][O:9][NH:10][C:11]([NH:13][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[NH:15])=[NH:12].C(O)C.[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31]>O>[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[O:5][CH2:6][CH2:7][CH2:8][O:9][NH:10][C:11]([NH:13][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[NH:15])=[NH:12].[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[O:5][CH2:6][CH2:7][CH2:8][O:9][NH:10][C:11]([NH:13][C:14]([NH:16][CH:17]([CH3:19])[CH3:18])=[NH:15])=[NH:12]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of453.6 g (1.252 moles) of 1-[3-(3,4-Dichlorophenoxy)propyloxy]-5-isopropylbiguanide, 1.0 L of ethanol and 74.4 g (0.630 moles) of succinic acid was heated to 60° C. to obtain a solution. A total of 500 ml of water was added dropwise at 60° C. After standing at room temperature for 15 hr the product was collected, washed with 300 mL of 50% ethanol cooled to 5° C. and dried at 105° C. for 3 hr to give 508 g (96.3%) mp 148.0-149.5°, 1H-NMR (DMSO-d6) δ1.00 (d,. 6H), 1.9 (m, 2H) 2.20 (s, 2H), 3.5-4.2, (m, 5H), 5.5 (br s, 2H), 6.7-7.5 (m, 4H), 8.1 (br s, 4H).

Workup

customto obtain a solution
customthe product was collected
washwashed with 300 mL of 50% ethanol
customdried at 105° C. for 3 hr
customto give 508 g (96.3%) mp 148.0-149.5°, 1H-NMR (DMSO-d6) δ1.00 (d,. 6H), 1.9 (m, 2H) 2.20 (s, 2H), 3.5-4.2, (m, 5H), 5.5 (br s, 2H), 6.7-7.5 (m, 4H), 8.1 (br s, 4H)

Sources & evidence

ORD record: ord-8d12334457b84eb38c23ff988d4e953a
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693217B2

Reaction notes

Loading…