Water → HCID 19100725, compound

HRID 1974991Notes

Reaction equation

HRID 1974991 reaction equation
[CH3:1][C:2]1[C:3]([NH:16][C:17]([O:19]C(C)(C)C)=O)=[C:4]([NH:8][C:9](OC(C)(C)C)=[O:10])[S:5][C:6]=1[CH3:7].C(OCC)(=O)C(OCC)=O.O>C(O)(=O)C>[CH3:7][C:6]1[S:5][C:4]2[NH:8][C:9](=[O:10])[C:17](=[O:19])[NH:16][C:3]=2[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 7268Diethyl OxalateHCID 19100743HCID 19100743, compound

Product 1

HCID 19100725HCID 19100725, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Crude di-t-butyl 4,5-dimethylthiophene-2,3-dicarbamate (9.7 g) was dissolved in 70 ml of acetic acid and 70 ml of diethyl oxalate and heated at reflux for three hours. 70 ml of water was added to the hot solution to precipitate the product. After 24 hours of stirring at room temperature the title compound was isolated by filtration, recrystallised from ethanol/acetic acid (65:35) to yield 1.5 g (41%) of crystals. M.p.>300° C. MS: 196. 1H-NMR (DMSO-D6, δ): 2.0 (s, 3H), 2.2 (s, 3H), 11.8 (s, 1H), 12.1 (s, 1H).

Workup

  1. temperatureat reflux for three hours
  2. customto precipitate the product
  3. customwas isolated by filtration
  4. customrecrystallised from ethanol/acetic acid (65:35)

Sources & evidence

ORD record
ord-41757a9327af4af0988c525a5e1d3db6
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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