4-Methylmorpholine → HCID 60402418, compound

HRID 1678466Notes

Reaction equation

HRID 1678466 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH:10]1([C:13](Cl)=[O:14])[CH2:12][CH2:11]1.CN1CCOCC1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13]([CH:10]2[CH2:12][CH2:11]2)=[O:14])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 77637Cyclopropanecarbonyl chlorideHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 60402418HCID 60402418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-4-methylaniline (100 mg), cyclopropanecarbonyl chloride (98 mg) and N-methylmorpholine (0.12 ml) in dry dichloromethane (2 ml) was stirred at 20 C for 18 h. The mixture was then partitioned between saturated sodium bicarbonate solution and dichloromethane. The dried extracts were evaporated giving a solid which was used without purification in the next synthetic step (120 mg).

Workup

  1. customThe mixture was then partitioned between saturated sodium bicarbonate solution and dichloromethane
  2. customThe dried extracts were evaporated
  3. customgiving a solid which
  4. customwas used without purification in the next synthetic step (120 mg)

Sources & evidence

ORD record
ord-0e0807077d1e4949830432f01adcbe09
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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