Potassium Hydroxide → HCID 19013472, compound

HRID 1729083Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][N:4]([C:7]1[CH:8]=[C:9]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1)[CH2:5][CH3:6].[OH-].[K+]>CO.O>[Cl:1][CH2:2][CH2:3][N:4]([C:7]1[CH:8]=[C:9]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1)[CH2:5][CH3:6]

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of (XIV; R=Z=H) (2.88 g, 8 mmol) in MeOH (100 mL) containing KOH (5.6 g) was stirred at 25° C. until homogeneous, andthen for a further 5 h. The mixture was diluted with water, filtered, and acidified with AcOH to give 4-[3-(N-(2-chloroethyl)-N-ethylamino) phenyl]carbamoylbenzenecarboxylic acid (XV; R=Z=H) (2.08 g, 75%), mp (EtOAc) 203° C. (dec.). 1H NMR (CD3SOCD3) 13.3 (br s, 1 H, COOH), 10.21 (s, 1 H, CONH), 8.05 (q, J=8.50, 4 H, H-2',3',5'6'), 7.16 (m, 3 H, H-2,4,6 ), 6.48 (m, 1 H, H-5), 3.72 (t, J=7.1Hz, 2 H, NCH2CH2Cl), 3.60 (t, J=7.1 Hz, 2 H, CH2Cl), 3.40(g, J=7.0 Hz, NCH2CH3)-, 1.12 (t, J=7.0 Hz, 3 H, CH3). Anal. (C18H19ClN2O3) C,H,N,Cl.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-073c088e56064b4e94c2ea66f0e87757
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05331004

Reaction notes

Loading…