Water → HCID 19100767, compound

HRID 1974988Notes

Reaction equation

HRID 1974988 reaction equation
C([O:5][C:6](=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]=1[NH:13][C:14](OC(C)(C)C)=[O:15])(C)(C)C.O>C(O)(=O)C.C(OCC)(=O)C(OCC)=O>[C:21]1([C:11]2[C:12]3[NH:13][C:14](=[O:15])[C:6](=[O:5])[NH:7][C:8]=3[S:9][CH:10]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86747563HCID 86747563, compound

Product 1

HCID 19100767HCID 19100767, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7268Diethyl OxalateSolvent

Procedure

Di-t butyl-4-phenylthiophene-2,3-dicarbamate (0.9 g crude oil from the preceding step) was dissolved in a mixture of 7 ml of acetic acid and 7 ml of diethyl oxalate and heated to reflux for three hours. While still hot, 7 ml of water was added, and the mixture stirred overnight at room temperature to precipitate 0.27 g of crude title compound. Three crystallisations from acetic acid combined with charcoal (Norit SU 18) and one from ethanol/acetic acid (1:1) produced 65 mg of pure title compound, m.p.>300° C. 1H-NMR (DMSO-D6, δ): 7.1 (s, 1H), 7.4 (m, 5H), 11.5 (br.s, 1H), 12.5 (br.s, 1H). MS: 244.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. customto precipitate 0.27 g of crude title compound
  4. customThree crystallisations from acetic acid

Sources & evidence

ORD record
ord-e31ec1cd50394c5f9dc3ef8b8c8f1c38
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

Loading…