Chloroacetonitrile → HCID 54120428, compound

HRID 1282796Notes

Reaction equation

HRID 1282796 reaction equation
[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].Cl[CH2:27][C:28]#[N:29].C(N(CC)CC)C.Cl.C(N(CC)CC)C>CC(C)=O>[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:24])(=[O:25])[NH2:23])[C:14]=1[O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]([O:11][CH2:27][C:28]#[N:29])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 54574929HCID 54574929, compound

Product 1

HCID 54120428HCID 54120428, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-n-butylthio-4-phenoxy-5-sulfamylbenzoic acid (2.3 g), chloroacetonitrile (1.4 g), triethylamine (0.61 g), and dry acetone (20 ml) is refluxed for 20 hours. After cooling the triethylamine hydrochloride formed is removed by filtration, and the filtrate is evaporated in vacuo. To the residue, water (35 ml) and ethylacetate (75 ml) are added, and the pH of the aqueous layer is adjusted to pH 7.5 by addition of 4 N hydrochloric acid. The organic layer is then separated, washed with diluted sodium hydrogen carbonate, dried and evaporated in vacuo. The residue is crystallized from chloroform petroleum ether to yield cyanomethyl 3-n-butylthio-4-phenoxy-5-sulfamylbenzoate with a melting point of 134°-135°C.

Workup

  1. temperatureis refluxed for 20 hours
  2. customformed
  3. customis removed by filtration
  4. customthe filtrate is evaporated in vacuo
  5. additionTo the residue, water (35 ml) and ethylacetate (75 ml) are added
  6. additionthe pH of the aqueous layer is adjusted to pH 7.5 by addition of 4 N hydrochloric acid
  7. customThe organic layer is then separated
  8. washwashed with diluted sodium hydrogen carbonate
  9. customdried
  10. customevaporated in vacuo
  11. customThe residue is crystallized from chloroform petroleum ether

Sources & evidence

ORD record
ord-ff292334ace142afb716f9907b7ecf0f
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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