Dimethyl Sulfoxide → HCID 13746709, compound

HRID 1731633Notes

Reaction equation

HRID 1731633 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[CH2:7][CH2:8][C:9]3[CH:15]=[C:14]([CH2:16][CH:17](C(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1)#[N:2].O.[Cl-].[Na+].CS(C)=O>C(Cl)Cl>[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[CH2:7][CH2:8][C:9]3[CH:15]=[C:14]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 13746705HCID 13746705, compound

Product 1

HCID 13746709HCID 13746709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 3-(7-cyano-10,11-dihydrodibenzo[b,f]thiepin-2-yl)-2-ethoxycarbonylpropanoate (4.025 g; 4.84 mmole), water (354 mg; 19.7 mmole), sodium chloride (576 mg) and dimethylsulfoxide (100 ml) are heated together under argon in an oil bath at 200°-205° C. for 3 hours. The cool reaction mixture was diluted with methylene chloride and the solution was extracted with water (3×100 ml), then dried (MgSO4) and evaporated to an oil (3.223 g; 97%). The pure title compound was obtained by short path distillation of the crude product (oven temperature 200° C./0.05 Torr).

Workup

  1. temperatureare heated together under argon in an oil bath at 200°-205° C. for 3 hours
  2. customThe cool reaction mixture
  3. extractionthe solution was extracted with water (3×100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to an oil (3.223 g; 97%)

Sources & evidence

ORD record
ord-f3df25def64440169914cda9500c78a3
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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