Bromoacetic Acid → Acetamide, 2-bromo-N-methyl-N-(2-methyl-6-benzoxazolyl)-

HRID 1428924Notes

Reaction equation

HRID 1428924 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.CCN=C=NCCCN(C)C.Cl.[Br:25][CH2:26][C:27]([OH:29])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[Br:25][CH2:26][C:27]([N:2]([CH3:1])[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1)=[O:29]

Participants

7

Reactant 3

HCID 6227Bromoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59594504HCID 59594504, compound

Product 1

HCID 90418141Acetamide, 2-bromo-N-methyl-N-(2-methyl-6-benzoxazolyl)-Yield 61%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N,2-dimethylbenzo[d]oxazol-6-amine (9.4 g, 58.0 mmol) in DCM (100 mL) was added EDC.HCl (26.6 g, 139 mmol), DMAP (0.354 g, 2.9 mmol) and bromoacetic acid (18.5 g, 133.0 mmol) at 0° C. under N2. The reaction mixture was stirred at rt overnight, then diluted with water (200 mL). The product was extracted with DCM (3×100 mL) and the organics were washed with brine, dried over Na2SO4 and concentrated to obtain 2-bromo-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (10.0 g, 61%), (MS: ESI +ve, 283.1 [M+H]); 1H NMR: (400 MHz, DMSO) δ: 2.59 (s, 3H), 3.23 (s, 3H), 4.04 (s, 2H), 6.76-6.74 (d, J=8.8, 1H), 7.38-7.30 (dd, J=8.8, 1H), 7.73-7.71 (d, J=8, 1H).

Workup

  1. extractionThe product was extracted with DCM (3×100 mL)
  2. washthe organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f294f6cacd274a30abbe1279aebce4ff
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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