Phosgene → 5-bromo-2-isocyanato-N,N-dimethyl-benzamide

HRID 2234674Notes

Reaction equation

HRID 2234674 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[C:14](Cl)(Cl)=[O:15]>ClCCl.C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1>[Br:13][C:10]1[CH:11]=[CH:12][C:2]([N:1]=[C:14]=[O:15])=[C:3]([CH:9]=1)[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

6

Reactant 2

HCID 6371PhosgeneHCID 509995122-Amino-5-bromo-N,N-dimethylbenzamide

Product 1

HCID 577316455-bromo-2-isocyanato-N,N-dimethyl-benzamide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-amino-5-bromo-N,N-dimethyl-benzamide (1.48 g, 6.09 mmol) was dissolved in a mixture of dichloromethane (60 mL) and saturated aqueous sodium bicarbonate (60 mL). 16 mL of 20% w/w phosgene in toluene was added and the mixture stirred at room temperature for 30 min. The layers were separated and the aqueous layer extracted three times with dichloromethane (20 mL). The combined organic layers were dried over sodium sulfate and evaporated. The residue was concentrated down several times from ether and dichloromethane to afford 5-bromo-2-isocyanato-N,N-dimethyl-benzamide as a yellow power. 1H-NMR (250 MHz, d6-DMSO) δ 7.95 (d, J=2.4 Hz, 1H), 7.80 (dd, J=6.3, 2.7 Hz, 1H), 7.16 (d, J=8.88 Hz, 1H), 3.10 (s, 6H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted three times with dichloromethane (20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated
  5. concentrationThe residue was concentrated down several times from ether and dichloromethane

Sources & evidence

ORD record
ord-033dfbf2ed8c4bfe85716706ddca032d
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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