1,1-Dichloroethane → HCID 14581394, compound

HRID 1935387Notes

Reaction equation

HRID 1935387 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([N:10]3[CH2:15][CH2:14][N:13](C)[CH2:12][CH2:11]3)=[CH:8][CH:7]=[CH:6][C:5]=12.Cl[C:18]([O:20][CH:21]=[CH2:22])=[O:19].ClC(Cl)C>>[N:1]1[S:2][N:3]=[C:4]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([C:18]([O:20][CH:21]=[CH2:22])=[O:19])[CH2:12][CH2:11]3)=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 78808Vinyl chloroformateHCID 145813934-(4-Methyl-1-piperazinyl)-2,1,3-benzothiadiazole

Product 1

HCID 14581394HCID 14581394, compound

Procedure

To a 25 ml round-bottomed flask equipped with condenser and nitrogen inlet were added 620 mg (2.64 mmol) of 4-(2,1,3-benzothiadiazolyl)-N-methylpiperazine, 0.224 ml (2.64 mmol) vinyl chloroformate, and 15 ml dichloroethane. The reaction was refluxed 16 hours, cooled, and evaporated. The residue was chromatographed on silica gel using methylene chloride/ethyl acetate as eluent, and the product fractions collected to give yellow solid 4-(2,1,3-benzothiadiazolyl)-N-vinyloxycarbonylpiperazine, 530 mg (69%). NMR (δ, CDCl3): 3.6 (m, 4H), 3.8 (m, 4H). 4.4-5.0 (m, 2H), 6.6-7.6 (m, 4H).

Workup

  1. customTo a 25 ml round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperatureThe reaction was refluxed 16 hours
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. customthe product fractions collected

Sources & evidence

ORD record
ord-7ad4e7cb62374a5ba7a91153b7cc16c0
Source dataset
uspto-grants-2002_05
Patent number
US06387904B2

Reaction notes

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