Ethane, 2-bromo-1,1-diethoxy- → HCID 12036785, compound

HRID 1875320Notes

Reaction equation

HRID 1875320 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH2:13])=[S:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14](OC(OCC)CBr)[CH3:15]>C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:14]=[CH:15][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2760234(p-Nitrophenyl)thiourea

Product 1

HCID 12036785HCID 12036785, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 1-(4-nitrophenyl)-2-thiourea (5.00 g, 25.4 mmol) in acetic acid (40 mL) was added bromoacetaldehyde diethyl acetal (3.94 mL, 25.4 mmol) at RT. The resulting mixture was heated to 100° C. for 2 h. After cooling to RT, the solvent was removed in vacuo. The residue was diluted with 1M NaOH (100 mL) and EtOAc (100 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated. Purification by column chromatography (20-80% EtOAc in hexanes) afforded the product as a yellow solid (2.75 g, 49%). 1H-NMR (400 MHz, DMSO-d6) δ 11.02 (s, 8.231H), 8.23 (d, J=9.3 Hz, 2H), 7.85 (d, J=9.3 Hz, 2H), 7.41 (d, J=3.6 Hz, 1H), 7.15 (d, J=3.6 Hz, 1H). LC/MS (10-99%) M/Z: M+1 obs=222.1; tR=2.50 min.

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with 1M NaOH (100 mL) and EtOAc (100 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×100 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated
  8. customPurification by column chromatography (20-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-97f73c41ec014c8b86bfc21063b9ad91
Source dataset
uspto-grants-2012_11
Patent number
US08309543B2

Reaction notes

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