Acetyl chloride → HCID 14579750, compound

HRID 1607295Notes

Reaction equation

HRID 1607295 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][N:6]([CH3:24])[C:7](=[S:23])[O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([CH2:16][CH2:17][CH3:18])=[C:11]([OH:19])[C:10]=1[C:20](=[O:22])[CH3:21].C(N(CC)CC)C>O1CCCC1.O.C(OCC)C>[CH3:24][N:6]([CH3:5])[C:7](=[S:23])[O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([CH2:16][CH2:17][CH3:18])=[C:11]([O:19][C:1](=[O:3])[CH3:2])[C:10]=1[C:20](=[O:22])[CH3:21]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14579749HCID 14579749, compound

Product 1

HCID 14579750HCID 14579750, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (1.9 g, 25 mmol) was added dropwise to an ice-cold stirring mixture of O-(2-acetyl-3-hydroxy-4-propyl-6-chlorophenyl) dimethylthiocarbamate (6.3 g, 20 mmol) (Step a) and triethylamine (3.0 g, 30 mmol) in tetrahydrofuran (50 mL) The mixture was stirred for 2 hours and then diluted with water and diethyl ether. The organic layer was separated, dried (MgSO4), filtered and concentrated to obtain the title compound as an oil which crystallized on standing. The crystals were slurried with hexane, filtered and dried to give the title compound, m.p. 86°-88° C.

Workup

  1. stirringwas stirred for 2 hours
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6baf9fe432f647909e61afcf59436b12
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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