Ammonium Chloride → HCID 178458297, compound

HRID 2082753Notes

Reaction equation

HRID 2082753 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=O)[CH2:2][CH3:3].C(O[CH:17]=[C:18]([C:24]#[N:25])[C:19]([O:21]CC)=O)C.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+:31]>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]1[NH:31][C:19](=[O:21])[C:18]([C:24]2[NH:25][N:28]=[N:27][N:26]=2)=[CH:17][N:9]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 430512-PropoxybenzamideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 178458297HCID 178458297, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (ice bath) solution of 2-n-propoxybenzamide (1.00 g., 5.61 mmoles) in dry N,N-dimethylformamide (4 ml.) was added ethyl ethoxymethylenecyanoacetate (0.94 g., 5.61 mmoles). Twenty minutes later sodium azide (0.447 g., 6.88 mmoles) and ammonium chloride (0.368 g., 6.88 mmoles were added. The ice bath was removed and the mixture heated by means of an oil bath maintained at 127° for 30 hours. The cooled mixture was poured into ice-water (400 ml.) and acidified with 6N hydrochloric acid. The collected solid (0.93 g.), m.p. 245°-248° (decomp) was recrystallized from 2-methoxyethanol to give the title compound (0.69 g., 41%) m.p. 256°-257° (decomp).

Workup

  1. addition, 6.88 mmoles were added
  2. customThe ice bath was removed
  3. temperaturethe mixture heated by means of an oil bath
  4. temperaturemaintained at 127° for 30 hours
  5. additionThe cooled mixture was poured into ice-water (400 ml.)
  6. customThe collected solid (0.93 g.), m.p. 245°-248° (decomp) was recrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-a4e9b9c9802a4914a47e84dfbcffc28c
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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