Dimethyl Sulfoxide → HCID 22241385, compound

HRID 892219Notes

Reaction equation

HRID 892219 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[C:40]([CH3:41])=[CH:39][CH:38]=[CH:37][C:14]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[O:20][CH2:21][C:22]1[N:31]([CH3:32])[C:30](=[O:33])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C(N(CC)CC)C>ClCCl>[CH3:41][C:40]1[CH:39]=[CH:38][CH:37]=[C:14]([CH2:15][O:16][C:17]2[CH:36]=[CH:35][CH:34]=[C:19]([O:20][CH2:21][C:22]3[N:31]([CH3:32])[C:30](=[O:33])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:18]=2)[C:13]=1[CH:12]=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22241343HCID 22241343, compound

Product 1

HCID 22241385HCID 22241385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of oxalyl chloride (2.5 mL, 1.75 M in CH2Cl2) is added, dropwise, DMSO (80 mL). On complete addition, a solution of 2-[3-(2-hydroxymethyl-3-methyl-1 benzyloxy)-phenoxymethyl]-3-methyl-3H-quinazolin-4-one (120 mg, 0.28 mmol, example 101) in dichloromethane (1 mL) is added dropwise. This solution is stirred for 5 min then triethylamine (276 mL, 2 mmol) is added in one portion. The cold bath is removed and stirring continued for 10 min. The mixture is then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated to give the title compound as a solid. MS (ESI) 415 (M+H)+.

Workup

  1. additionis added
  2. additionOn complete addition
  3. customThe cold bath is removed
  4. stirringstirring
  5. waitcontinued for 10 min
  6. additionThe mixture is then diluted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-13be80ba75b14c159c8ef917847a14be
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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