Acetic Anhydride → N-(1,1-dimethylethyl)-N-(3,3,3-trichloro-2-hydroxypropyl)acetamide

HRID 127956Notes

Reaction equation

HRID 127956 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])([CH3:4])[CH3:3].[C:13](OC(=O)C)(=[O:15])[CH3:14]>ClCCl>[CH3:4][C:2]([N:5]([CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])[C:13](=[O:15])[CH3:14])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 234710203-(Tert-butylamino)-1,1,1-trichloropropan-2-ol

Product 1

HCID 23471021N-(1,1-dimethylethyl)-N-(3,3,3-trichloro-2-hydroxypropyl)acetamideYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 5 grams of 3-(1,1-dimethylethylamino)-1,1,1-trichloro-2-propanol in 75 grams of dichloromethane at -60° C., 2.2 grams of acetic anhydride was added dropwise during 15 minutes. After the reaction mixture was allowed to warm to ambient temperature during 1 hour, the mixture was stirred for 2 hours. The solution was washed with 100 grams of saturated aqueous sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under a reduced pressure of 100 mm. Hg to 3.9 grams of an oil. The oil was crystallized from methylcyclohexane to yield 1.4 gram of white N-(1,1-dimethylethyl)-N-(3,3,3-trichloro-2-hydroxypropyl)acetamide melting 124°-126° C.

Workup

  1. washThe solution was washed with 100 grams of saturated aqueous sodium bicarbonate
  2. dry with materialdried with anhydrous sodium sulfate
  3. customevaporated under a reduced pressure of 100 mm. Hg to 3.9 grams of an oil
  4. customThe oil was crystallized from methylcyclohexane

Sources & evidence

ORD record
ord-1dc817b4c40a4917bfc9a7b7ad20d94b
Source dataset
uspto-grants-1981_03
Patent number
US04258060

Reaction notes

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