Ammonia → HCID 54454820, compound

HRID 1730735Notes

Reaction equation

HRID 1730735 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16][CH2:17][C:18]([OH:20])=O)[CH3:15])=[CH:10][CH:9]=1.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.N.[N-]1C=CN=C1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16][CH2:17][C:18]([NH2:23])=[O:20])[CH3:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 20348746HCID 20348746, compound

Product 1

HCID 54454820HCID 54454820, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

63.0 gm (0.205 mol) of [1-(2'-chloro-4-biphenylyl)-ethylthio]-acetic acid were dissolved in 630 ml of dry tetrahydrofuran, and 33.3 gm (0.246 mol) of carbonyldiimidazole were added. After stirring the mixture for 1/2 hour, dry ammonia was introduced into 300 ml of the obtained solution of the imidazolide (corresponding to 0.0683 mol), while cooling slightly, until the mixture was saturated. Subsequently, the mixture was stirred for 2.5 hours more and then evaporated in vacuo. The residue was distributed between water and ethyl acetate, and washed several times with dilute hydrochloric acid. The organic layer was dried and evaporated. Yield: 100% of theory; oil, Rf -value: 0.2 on carrier 1 with cyclohexane/ethyl acetate = 1:1.

Workup

  1. temperaturewhile cooling slightly, until the mixture
  2. stirringSubsequently, the mixture was stirred for 2.5 hours more
  3. customevaporated in vacuo
  4. washwashed several times with dilute hydrochloric acid
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-aff34e39a5284f22aa2e18bbf7c97224
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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