Dimethylformamide → N'-[2-Carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine

HRID 612063Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[CH3:30][N:31]([CH:33]=O)[CH3:32]>C(Cl)Cl>[C:4]([C:3]1[CH:9]=[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:12][C:2]=1[N:1]=[CH:30][N:31]([CH3:33])[CH3:32])([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 55 °C

Procedure

To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (Pfizer patent WO 96130347) in 50 ml of DMF at 0° C. was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55° C. for 45 m, cooled, diluted with methylene chloride, and treated at 0° C. with 200 ml of N/i sodium hydroxide during 2 m. The organic layer was separated and washed at 0° C. with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) δ 3.02 (s, Me2N).

Workup

temperaturecooled
customThe organic layer was separated
washwashed at 0° C. with water
customThe solution was dried
customevaporated with added toluene present

Sources & evidence

ORD record: ord-729b666d0249474c800fee3e58234841
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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