Acetic Acid → 2-Chloro-N-(4-methyltetrahydro-2H-pyran-4-yl) acetamide

HRID 456734Notes

Reaction equation

[CH3:1][C:2]1(O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(O)(=[O:11])C.S(=O)(=O)(O)O.[Cl:18][CH2:19][C:20]#[N:21]>>[Cl:18][CH2:19][C:20]([NH:21][C:2]1([CH3:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)=[O:11]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 1118Sulfuric Acid

HCID 7856Chloroacetonitrile

HCID 123471184-Methyloxan-4-ol

Product 1

HCID 184373262-Chloro-N-(4-methyltetrahydro-2H-pyran-4-yl) acetamide

Procedure

To a solution of 4-methyltetrahydro-2H-pyran-4-ol obtained in Example 7-1 in chloroacetonitrile (0.65 mL), was added a mixture of acetic acid and conc. sulfuric acid (1/1, 1.6 mL) dropwise with cooling on an ice bath. The reaction mixture was warmed to room temperature and stirred for 3 hrs.

Workup

temperaturewith cooling on an ice bath

Sources & evidence

ORD record: ord-194497308cdf495f949142f79cca5feb
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186731B2

Reaction notes

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