Acetic Acid → HCID 57691901, compound

HRID 550550Notes

Reaction equation

HRID 550550 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.[CH3:8][NH:9][C:10]([NH:12][NH2:13])=[S:11].C(O)(=O)C>CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:9]([CH3:8])[C:10](=[S:11])[NH:12][N:13]=1

Participants

5

Reactant 3

HCID 176Acetic Acid3×HCID 10953Delta-ValerolactoneHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 57691901HCID 57691901, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Tetrahydro-2H-pyran-2-one (2 ml), N-methylhydrazinecarbothioamide (3.4 g) and acetic acid (0.3 ml) were suspended in methanol (10 ml). The reaction was heated in microwave oven at 120° C. for 20′ followed by further 10′ at 110° C. Acetic acid was added (0.3 ml) and reaction was heated in a microwave oven at 140° C. for 20′, further acetic acid (0.3 ml) was added and the reaction was in a microwave oven at 140° C. for 20′. The solvent was removed under reduced pressure, DCM was added to the crude and solid filtered-off. Solvent was removed under reduced pressure to give a crude product that was purified by flash chromatography on silica gel (DCM/MeOH from 0 to 10%) to give the title compound as a white solid (1 g).

Workup

  1. customat 110° C
  2. custom(0.3 ml) and reaction
  3. additionwas added
  4. customthe reaction was in a microwave oven at 140° C. for 20
  5. customThe solvent was removed under reduced pressure, DCM
  6. additionwas added to the crude and solid filtered-off
  7. customSolvent was removed under reduced pressure
  8. customto give a crude product that
  9. customwas purified by flash chromatography on silica gel (DCM/MeOH from 0 to 10%)

Sources & evidence

ORD record
ord-266297101bcb4ecebaa586908cb50183
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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