Aniline → 2-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid phenylamide

HRID 1938143Notes

Reaction equation

HRID 1938143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=1.O=S(Cl)Cl.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])[N:10]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 214686062-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid

Product 1

HCID 214686052-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid phenylamideYield 82.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g (3.75 mmol) 2-(3-chlorophenoxy)thiazole-4-carboxylic acid was added to 1 ml of SOCl2 and refluxed until the mixture gave a clear solution. Excess SOCl2 was evaporated in vacuo and the remaining acid chloride dissolved in 25 ml toluene. To this solution was added a solution of 0.34 g (3.65 mmol) aniline and 0.37 g triethylamine in 20 ml toluene. After stirring over night at room temperature the solution was washed with 20 ml dil. HCl, 20 ml water, 20 ml dil. NaOH and 20 ml water. The organic layer was dried with NaSO4 and evaporated to dryness to give 1.0 g (82.8%) 2-(3-chlorophenoxy)thiazole-4-carbanilide (m.p.:94°-95° C.).

Workup

  1. temperaturerefluxed until the mixture
  2. customgave a clear solution
  3. customExcess SOCl2 was evaporated in vacuo
  4. dissolutionthe remaining acid chloride dissolved in 25 ml toluene
  5. washwas washed with 20 ml dil. HCl, 20 ml water, 20 ml dil. NaOH and 20 ml water
  6. dry with materialThe organic layer was dried with NaSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c26bab45565b4221b792717c56a187d9
Source dataset
uspto-grants-1997_12
Patent number
US05693594

Reaction notes

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