Propan-2-one--dichloromethane (1/1) → HCID 69893862, compound

HRID 2307896Notes

Reaction equation

HRID 2307896 reaction equation
C(Cl)Cl.[CH3:4][C:5]([CH3:7])=O.N1([C:13]2[CH:34]=[CH:33][C:16]([CH2:17][CH2:18][C:19]([NH:21][CH:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:20])=[CH:15][CH:14]=2)C=CC=C1>>[N:21]1([C:19]([C:13]2[CH:14]=[CH:15][C:16]([CH2:17][CH2:18][C:19]([NH:21][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:20])=[CH:33][CH:34]=2)=[O:20])[CH:22]=[CH:7][CH:5]=[CH:4]1

Participants

3

Reactant 2

HCID 21584124Propan-2-one--dichloromethane (1/1)HCID 53649664HCID 53649664, compound

Product 1

HCID 69893862HCID 69893862, compound

Procedure

4.6 g of diethyl 4-aminobenzylacetamidomalonate in 104 ml of acetic acid are placed in a three-necked flask which is maintained under nitrogen. 7.02 g of sodium acetate are added, followed by 1.87 ml of 2,5-dimethoxytetrahydrofuran. The mixture is heated at 65° C. for 1 h 15 min, then cooled down and extracted with 100 ml of dichloromethane and 100 ml of distilled water. The aqueous phase is separated off after settling and then washed with 3 times 100 ml of dichloromethane. The organic phases are combined, washed with 100 ml of water and then with 100 ml of a saturated solution of NaCl, separated off after settling and then dried over magnesium sulphate; the phases are filtered and then evaporated to dryness under reduced pressure (50 kPa) in order to yield 6.2 g of a solid which is purifed by flash chromatography (eluent CH2Cl2/acetone 75/25 by volume). This results in 3.57 g of diethyl 4-(1-pyrrolyl)benzylacetamidomalonate in the form of a beige solid which melts at 110° C.

Sources & evidence

ORD record
ord-6d845a1d1b984342be7eae74ab9779c0
Source dataset
uspto-grants-2004_12
Patent number
US06833382B2

Reaction notes

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