Chloroacetonitrile → HCID 21438990, compound

HRID 329198Notes

Reaction equation

HRID 329198 reaction equation
[C:1]([NH:6][C:7](=[S:15])[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([O:3]CC)=O.CC[O-].[K+].Cl[CH2:21][C:22]#[N:23]>CO>[CH:9]1([O:8][C:7]2[S:15][C:21]([C:22]#[N:23])=[C:1]([OH:3])[N:6]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 23670592Potassium ethoxideHCID 53693398HCID 53693398, compound

Product 1

HCID 21438990HCID 21438990, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 38.3 g of cyclohexyl N-carbethoxy-thiocarbamate and 11.56 g of potassium ethylate in 400 ml of methanol was stirred for 2 hours and 12.45 g of chloroacetonitrile were added thereto. The mixture was stirred for 48 hours at room temperature and was then concentrated to dryness. The residue was added to water and the aqueous phase was acidified with hydrochloric acid. The aqueous phase was extracted with ether and the ether phase was dried and concentrated to dryness to obtain 15 g of 2-cyclohexyloxy-4-hydroxy-5-cyanothiazole in the form of white crystals melting at 138° C.

Workup

  1. stirringThe mixture was stirred for 48 hours at room temperature
  2. concentrationwas then concentrated to dryness
  3. additionThe residue was added to water
  4. extractionThe aqueous phase was extracted with ether
  5. dry with materialthe ether phase was dried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-41e5b5170ad14c9e836b0918f2446005
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

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