Dimethylformamide → HCID 66907841, compound

HRID 909401Notes

Reaction equation

HRID 909401 reaction equation
Br[CH2:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])[N:8]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:5]=2[CH:4]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].CN(C)C=O.C(OCC)(=O)C>O.C(Cl)Cl>[CH2:32]([N:34]([CH2:2][C:3]1[CH:31]=[CH:30][C:6]2[C:7](=[O:29])[N:8]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][C:5]=2[CH:4]=1)[CH2:35][CH3:36])[CH3:33]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 25064370HCID 25064370, compound

Product 1

HCID 66907841HCID 66907841, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

30.0 g of 6-(bromomethyl)-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one and 13.9 mL of diethylamine were added to 90 mL of N,N-dimethylformamide. This was stirred for 50 minutes at room temperature. Ethyl acetate, methylene chloride and water were added to the reaction mixture, and an organic layer was separated. Water and hydrochloric acid were added to the organic layer, and an aqueous layer was separated. An organic layer was extracted with water and, together with the aqueous layer, 180 mL of acetone was added and 13 mL of a 20% sodium hydroxide aqueous solution was added dropwise. Solids were filtered to obtain 22.2 g of 6-(diethylamino)methyl-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one was obtained in the form of a pale yellowish-white solid.

Workup

  1. customan organic layer was separated
  2. additionWater and hydrochloric acid were added to the organic layer
  3. customan aqueous layer was separated
  4. extractionAn organic layer was extracted with water and, together with the aqueous layer, 180 mL of acetone
  5. additionwas added
  6. addition13 mL of a 20% sodium hydroxide aqueous solution was added dropwise
  7. filtrationSolids were filtered

Sources & evidence

ORD record
ord-d8730ba62e7c4f8db23ad76bb441acaf
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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