1,1'-Carbonyldiimidazole → 4-Methyl-3H-benzooxazol-2-one

HRID 1846462Notes

Reaction equation

HRID 1846462 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].CCN(C(C)C)C(C)C.C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>ClCCl>[CH3:9][C:3]1[C:2]2[NH:1][C:24](=[O:25])[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 30141382-Amino-m-cresol

Product 1

HCID 127093364-Methyl-3H-benzooxazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50.0 g (0.39 mol) 2-amino-m-cresol and 0.21 L (1.23 mol) DIPEA in 400 mL dichloromethane were cooled to 0° C. A mixture of 76.0 g (0.45 mol) CDI in 1.2 L dichloromethane was added dropwise and stirred overnight at RT. The reaction mixture was washed with a 1M KHSO4 solution and water. The organic phase was separated off and evaporated down i.vac. The residue was combined with boiling ethyl acetate and while the mixture cooled PE was added dropwise. The precipitate formed was suction filtered, washed with PE and dried.

Workup

  1. additionwas added dropwise
  2. washThe reaction mixture was washed with a 1M KHSO4 solution and water
  3. customThe organic phase was separated off
  4. customevaporated down i.vac
  5. temperaturecooled PE
  6. additionwas added dropwise
  7. customThe precipitate formed
  8. filtrationfiltered
  9. washwashed with PE
  10. customdried

Sources & evidence

ORD record
ord-9de03ec7730b404ea84627a7b5275141
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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