Diethyl Oxalate → Acea 1011

HRID 53697Notes

Reaction equation

HRID 53697 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:13]=1[NH2:23]>>[Cl:22][C:14]1[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=[C:12]2[C:13]=1[NH:23][C:2](=[O:4])[C:1](=[O:8])[NH:11]2

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 7357843-Chloro-5-(trifluoromethyl)benzene-1,2-diamine

Product 1

HCID 127872Acea 1011Yield 50.9%

Conditions

Temperature
180 °C

Procedure

439.0 mg (3.0 mmol) of diethyl oxalate (from Sigma, used as received) was added to 210.6 mg (1.0 mmol) of 1,2-diamino-3-chloro-5trifluoromethylbenzene (from PCR Inc., used as received), and the resulting yellow solution was heated at 180° C. (bath temperature) under Ar with stirring for 3.5 h, the solution became thick with formation of cream precipitate and hard to stir. The reaction mixture was allowed to cool to r.t., and triturated with hexane (10 mL). The precipitate was collected by vacuum filtration, washed with hexane (2×10mL) (the combined hexane filtrate was saved), dried under 0.1 mmHg for 4 h affording 134.6 mg (58%) of the crude desired product as a yellow powder (95-98% pure by NMR), mp.330°-2° C. (dec.) (preheated block).

Workup

  1. stirringhard to stir
  2. temperatureto cool to r.t.
  3. customtriturated with hexane (10 mL)
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with hexane (2×10mL) (the combined hexane filtrate
  6. customdried under 0.1 mmHg for 4 h

Sources & evidence

ORD record
ord-adf16db549364ad9a928d77f9c830ffa
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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