3-Chloro-2-hydroxypropylmethacrylate → N-(2,3-Dihydroxypropyl) 5-Phenyltetrazole

HRID 623232

Reaction equation

HRID 623232 reaction equation
C([O:6][CH2:7][CH:8]([OH:11])[CH2:9]Cl)(=O)C(C)=C.[C:12]1([C:18]2[NH:22][N:21]=[N:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na]>COCCO>[OH:11][CH:8]([CH2:7][OH:6])[CH2:9][N:22]1[C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:19][N:20]=[N:21]1

Participants

4

Reactant 2

HCID 1144703-Chloro-2-hydroxypropylmethacrylateHCID 178507078HCID 178507078, compound

Product 1

HCID 13285687N-(2,3-Dihydroxypropyl) 5-Phenyltetrazole

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3-chloro-2-hydroxypropyl methacrylate (0.50 mole; 89.3 g. and 500 ppm 4-methoxyphenol as inhibitor) in 2-methoxyethanol (300 ml) was added to sodium 5-phenyltetrazole (1.0 mole; 168.2 g) dissolved in 2-methoxyethanol (800 ml) and heated at 100° C. for 14.5 hours. The product solution was quenched with H2O (150 ml), extracted with CH2Cl2 (3×500 ml), the extracts washed with H2O (500 ml) and concentrated to a semi-solid, m.p. 25°-115° C, gas evolution, 219° C.

Workup

  1. customThe product solution was quenched with H2O (150 ml)
  2. extractionextracted with CH2Cl2 (3×500 ml)
  3. washthe extracts washed with H2O (500 ml)
  4. concentrationconcentrated to a semi-solid, m.p. 25°-115° C, gas evolution, 219° C.

Sources & evidence

ORD record
ord-8e8cfecbfcf947ae938ef70d579bfc68
Source dataset
uspto-grants-1988_09
Patent number
US04774266

Linked notes

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