Dimethylformamide → HCID 18929201, compound

HRID 1490294Notes

Reaction equation

HRID 1490294 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].CN(C=O)C.O1CCOCC1.[Br:23][CH2:24][C:25](Br)=[O:26]>O>[Cl:11][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][C:25](=[O:26])[CH2:24][Br:23])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 61147Bromoacetyl bromideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 18929201HCID 18929201, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-6-chlorobenzoic acid (10 g, 0.06 mol), anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) was cooled to 0° C. in 300 mL 3-necked flask fitted with a magnetic stirrer and constant additional funnel. Bromoacetyl bromide was added dropwise over a 20-25 min period keeping the internal temperature between 0° to 1° C. After the addition was completed, the solution was allowed to warm to room temperature and stirring was continued for 20 h. The reaction mixture was cooled in an ice-bath and diluted with water (150 mL). The resulting yellow crystalline product was filtered, washed sequentially with 5% HBr solution (50 mL), water (50 mL), and then dried in vacuum oven (20 h, 40°-45° C.) to afford 5 g (30%) of the title compound, mp 133°-135° C. (decomp.); 1H NMR (CD3OD) 7.70 (d, 1H, J=8), 7.43 (t, 1H, J=8.4), 7.35 (d, 1H, J=8), 4.05 (s, 2H); 13C NMR (CD3OD) δ 168.19, 167.84, 137.24, 133.31, 132.85, 132.08, 128.78, 128.21, 124.20, 29.21; MS (EI, m/z) 293 (M+).

Workup

  1. customfitted with a magnetic stirrer and constant additional funnel
  2. custombetween 0° to 1° C
  3. additionAfter the addition
  4. temperatureThe reaction mixture was cooled in an ice-bath
  5. filtrationThe resulting yellow crystalline product was filtered
  6. washwashed sequentially with 5% HBr solution (50 mL), water (50 mL)
  7. customdried in vacuum oven (20 h, 40°-45° C.)

Sources & evidence

ORD record
ord-9fcd7059007944eca526fe37423b0ba6
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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