Hexane → HCID 178470096, compound

HRID 1722071Notes

Reaction equation

HRID 1722071 reaction equation
[F:1][C:2]1[C:30]([F:31])=[C:29]([F:32])[CH:28]=[CH:27][C:3]=1[NH:4][C:5](=[C:16]([C:22](OCC)=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:23][C:22]1[C:27]2[C:3](=[C:2]([F:1])[C:30]([F:31])=[C:29]([F:32])[CH:28]=2)[N:4]=[C:5]([S:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 8058HexaneHCID 14673304Diethyl [(2,3,4-trifluoroanilino)(p-methoxybenzylthio)methylene]malonate

Product 1

HCID 178470096HCID 178470096, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent2×

Procedure

A solution of diethyl [(2,3,4-trifluoroanilino)(p-methoxybenzylthio)methylene]malonate (80.9 g) in diphenyl ether (60 ml) heated at 110° C. was added dropwise to diphenyl ether (210 ml) kept at 250° to 260° C. with stirring under nitrogen stream over a period of 15 minutes. After the reaction mixture was further stirred at the same temperature for 5 minutes, the mixture was cooled to room temperature and added to hexane (3000 ml). The resulting precipitate was filtered to give the title compound (59.9 g), which was recrystallized from ethyl acetate to give yellow crystals, m.p. 174°-176° C.

Workup

  1. customkept at 250° to 260° C.
  2. stirringAfter the reaction mixture was further stirred at the same temperature for 5 minutes
  3. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-28d48a26bce1447c8d43b1789585e0bc
Source dataset
uspto-grants-1989_08
Patent number
US04853469

Reaction notes

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