Aniline → HCID 20376606, compound

HRID 2052425Notes

Reaction equation

HRID 2052425 reaction equation
NC1C=CC=CC=1.[CH:8]([S:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])([CH3:10])[CH3:9].C(N(CC)CC)C.[CH3:30][C:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>O1CCCC1>[CH:8]([S:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:34]([C:31]2([CH3:30])[CH2:33][CH2:32]2)=[O:35])=[CH:14][C:13]=1[C:19]([F:22])([F:20])[F:21])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 20376627HCID 20376627, compound

Product 1

HCID 20376606HCID 20376606, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution containing 23.5 g (0.1 mole) of the aniline prepared in (b) above and 10.1 g (0.1 mole) of triethylamine in 150 ml of tetrahydrofuran was added dropwise over 5 minutes 11.9 g (0.1 mole) of 1-methylcyclopropylcarboxylic chloride. This addition was exothermic to 55° C. The mixture was refluxed for 1 hour, poured into ice water and filtered. The filter cake was recrystallized from hexane to give 25 g (79%) of product as a colorless crystalline solid, m.p. 103°-105° C.

Workup

  1. additionThis addition
  2. customwas exothermic to 55° C
  3. temperatureThe mixture was refluxed for 1 hour
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from hexane

Sources & evidence

ORD record
ord-56b11b70c3cd43ab9adf04ece0a96bea
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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