Diethyl Ether → HCID 19001538, compound

HRID 2259656Notes

Reaction equation

HRID 2259656 reaction equation
[OH:1][CH:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][CH2:5]O.[CH2:25]([N:27](CC)CC)C.CS(Cl)(=O)=O.C(OCC)C>C(Cl)Cl>[OH:1][CH:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][CH2:5][C:25]#[N:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19001539HCID 19001539, compound

Product 1

HCID 19001538HCID 19001538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 g of the 3-[2-(1,4-dihydroxybutyl)benzothiazol-6-yl]-5-methoxymethyl-2-oxazolidinone thus obtained was dissolved in 20 ml of anhydrous methylene chloride and 1 ml of anhydrous triethylamine was added to the solution. 0.6 ml of methanesulfonyl chloride was slowly added to the solution under cooling with ice. After stirring for 30 min, 100 ml of diethyl ether was added to the reaction mixture. An insoluble matter was filtered off and then the solvent was distilled off. The resulting crude product was dissolved in 15 ml of dimethyl sulfoxide. 1.5 g of potassium cyanide was added to the solution and a reaction was conducted at 80° C. for 8 h. After cooling the reaction liquid followed by ordinary treatment and purification, 1.5 g of the titled compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. filtrationAn insoluble matter was filtered off
  3. distillationthe solvent was distilled off
  4. dissolutionThe resulting crude product was dissolved in 15 ml of dimethyl sulfoxide
  5. addition1.5 g of potassium cyanide was added to the solution
  6. waita reaction was conducted at 80° C. for 8 h
  7. temperatureAfter cooling
  8. customthe reaction liquid
  9. customfollowed by ordinary treatment and purification

Sources & evidence

ORD record
ord-6d71fd0cc6e74c14a6e976c75b69dd31
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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