Water → p-Chlorophenyl-5-methoxymethyl oxazolidine

HRID 1413321Notes

Reaction equation

HRID 1413321 reaction equation
[NH2:1][CH2:2][CH:3]([OH:7])[CH2:4][O:5][CH3:6].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.O>C1C=CC=CC=1>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]2[NH:1][CH2:2][CH:3]([CH2:4][O:5][CH3:6])[O:7]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 1245101-Amino-3-methoxypropan-2-ol

Product 1

HCID 20291464p-Chlorophenyl-5-methoxymethyl oxazolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Twelve and six tenths (12.6) grams of 1-amino-3-methoxy-2-propanol and 16.9 grams of p-chlorobenzaldehyde were combined in 150 milliliters of benzene and heated to reflux under a modified Dean-Stark apparatus until about 2.5 milliliters of water were azeotropically removed. An additional 50 milliliters of benzene was distilled over and the mixture was cooled to room temperature and the volume was adjusted to 109.2 milliliters, so that 4 milliliters=1 gram of intermediate. Aliquots of this solution were used in subsequent reactions.

Workup

  1. temperatureheated
  2. customwere azeotropically removed
  3. distillationAn additional 50 milliliters of benzene was distilled over and the mixture

Sources & evidence

ORD record
ord-35d95240b84540b8ac36cee8bc7d2717
Source dataset
uspto-grants-1981_02
Patent number
US04249931

Reaction notes

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