Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 67820322, compound

HRID 1491562Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=2)[C:11]=1[CH:12]=O)=[O:5])[CH3:2].Cl.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][NH2:38])=[CH:33][CH:32]=1.C([O-])(=O)C.[Na+]>C(Cl)Cl>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][N:38]=[CH:12][C:11]2[C:14]([O:18][C:19]3[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=3)=[CH:15][CH:16]=[CH:17][C:10]=2[O:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 2.93 g (7.5 mmol) of 2-(3-ethoxycarbonyl-propoxy)-6-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde (cf. Example 1), 1.5 g (8.3 mmol) of 4-chloro-phenylhydrazine-hydrochloride, 0.76 g(9.3 mmol) of sodium acetate and 150 ml of methylene chloride is stirred at 20° C. for 15 hours, then washed with saturated disodium hydrogen phosphate solution, dried with sodium sulphate and filtered. The filtrate is concentrated, the residue is stirred with methanol and the crystalline product is isolated by filtering off with suction. 2.6 g (67% of theory) of 2-(3-ethoxycarbonyl-propoxy)-6-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde-4-chloro-phenylhydrazone of melting point 139° C. are obtained.

Workup

washwashed with saturated disodium hydrogen phosphate solution
dry with materialdried with sodium sulphate
filtrationfiltered
concentrationThe filtrate is concentrated
stirringthe residue is stirred with methanol
customthe crystalline product is isolated
filtrationby filtering off with suction

Sources & evidence

ORD record: ord-f2ce11b679404cb5b27dbaf44e9ed999
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05371062

Reaction notes

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