Hydrochloric Acid → HCID 66987245, compound

HRID 2109505Notes

Reaction equation

HRID 2109505 reaction equation
[C:1]([NH:9][C:10](=[CH:15][N:16]([CH3:18])C)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:26]=[CH:25]C(N)=[CH:22][CH:21]=1.Cl>C(O)(C)C>[C:1]([NH:9][C:10](=[CH:15][NH:16][C:18]1[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 3644677HCID 3644677, compound

Product 1

HCID 66987245HCID 66987245, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
10 °C

Procedure

10g (39.5 mmol) of methyl 2-benzoylamino-3-dimethylaminoacrylate and 11.4 ml (118 mmol) of 4-fluoroaniline were dissolved in 200 ml of isopropanol at 40° C. The solution was admixed with 3.6 ml (43.5 mmol) of concentrated hydrochloric acid within 5 minutes (min) and stirred for a further 30 min. The suspension was cooled to 10° C. and the crystallized product was filtered off. Yield: 12.4 g (94% of theory) 1H NMR: 3.62 (s, 3H); 7.05-7.24 (m, 4H); 7.48-7.52 (m, 3H); 7.88 (d, 1H); 8.00-8.04 (m, 2H); 8.90 (d, 1H); 9.15 (s, 1H)

Workup

  1. filtrationthe crystallized product was filtered off

Sources & evidence

ORD record
ord-fa4001c65d9f49e6b4c2478e662f7f09
Source dataset
uspto-grants-2009_04
Patent number
US07514578B2

Reaction notes

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