Diethyl Oxalate → Acea 1011

HRID 439418Notes

Reaction equation

HRID 439418 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-5-trifluoromethylbenzene (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 (2×10 mL) (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 (2×10 mL) (the combined hexane filtrate
  6. customdried under 0.1 mmHg for 4 h

Sources & evidence

ORD record
ord-d741f4a5407c4e5b845d35dde12ef6d7
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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