Ethanol → S 8660

HRID 1723338Notes

Reaction equation

HRID 1723338 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=O)[C:5](=[O:11])[NH:6]2.[CH3:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=O.C(NCC)C.C([OH:36])C>>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([C:15]2[C:14]([CH3:13])=[C:4]([C:5]([OH:11])=[O:36])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])[N:6]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8021DiethylamineHCID 95230Propiophenone, 4'-phenyl-HCID 960474-Chloroisatin

Product 1

HCID 130331S 8660Yield 58%

Procedure

A mixture of 4-chloroisatin (7.28 g, 0.04 mol), [J. Am. Chem. Soc., 1251 (1956)], 4-phenylpropiophenone (8.8 g, 0.04 mol), diethylamine (4 ml, 0.04 mol) and ethanol (200 ml) was stirred for a period of 18 hours at room temperature. The precipitated solids were collected by filtration, washed with ice-cold ethanol and air dried to yield the adduct (9.1 g, 58%) m.p. 209°-214° dec.

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. washwashed with ice-cold ethanol and air
  3. customdried

Sources & evidence

ORD record
ord-fa474fecc33443c28aaea5f1eec22324
Source dataset
uspto-grants-1989_08
Patent number
US04861783

Reaction notes

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