Aniline → HCID 20376624, compound

HRID 2052429Notes

Reaction equation

HRID 2052429 reaction equation
NC1C=CC=CC=1.[CH3:8][N:9]([CH3:24])[S:10]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11].C(N(CC)CC)C.[CH3:32][C:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>O1CCCC1>[CH3:8][N:9]([CH3:24])[S:10]([C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:36]([C:33]2([CH3:32])[CH2:35][CH2:34]2)=[O:37])=[CH:15][C:14]=1[C:20]([F:21])([F:23])[F:22])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 20376640HCID 20376640, compound

Product 1

HCID 20376624HCID 20376624, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.7 g (0.025 mole) of the aniline prepared as in (c) above and 2.5 g of triethylamine in 50 ml of tetrahydrofuran was added dropwise 3.0 g (0.025 mole) of 1-methylcyclopropanecarboxylic chloride. The mixture was refluxed for one hour, poured into ice water, filtered and recrystallized from methanol to give 7.5 g (86%) of product as a white crystalline solid; m.p. 153°-156° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationfiltered
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-af7821ecbb7f4e788f19c92804d6cc3c
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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