Acetone Cyanohydrin → HCID 20062230, compound

HRID 1084625Notes

Reaction equation

HRID 1084625 reaction equation
CC1(C)C(=O)C=C(O[C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])CS1.C(N([CH2:28][CH3:29])CC)C.[CH3:30]C(C)(O)C#N.[S:36]1C[C:40](=[O:42])[CH2:39][C:38](=[O:43])[CH2:37]1>C(#N)C>[CH3:30][C:28]1([CH3:29])[C:40](=[O:42])[CH:39]([C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[C:38](=[O:43])[CH2:37][S:36]1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 3252862H-Thiopyran-3,5(4H,6H)-dioneHCID 20062229HCID 20062229, compound

Product 1

HCID 20062230HCID 20062230, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,2-dimethyl-5-(4-chloro-2-nitrobenzoyloxy)-3,6-dihydro-2H-thiopyran-3-one (8.3 g, 24.3 mmol), triethylamine (6.8 ml, 48.7 mmol) and acetone cyanohydrin (0.5 ml) in 35 ml of acetonitrile is stirred at RT for 16 hours. The reaction mixture is concentrated and taken up in ether. The ether extracts are washed with dilute HCl and with brine, dried and evaporated to dryness. The crude product is purified to give 2-2-dimethyl.4.(4.chloro.2.nitrobenzoyl).2H-thiopyran-3,5-(4H,6H)-dione (compound 1, Table A).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washThe ether extracts are washed with dilute HCl and with brine
  3. customdried
  4. customevaporated to dryness
  5. customThe crude product is purified
  6. customto give 2-2-dimethyl

Sources & evidence

ORD record
ord-b93720fd134c41ebb8e42c9d02b653f1
Source dataset
uspto-grants-1991_04
Patent number
US05006150

Reaction notes

Loading…