Methyl chloroformate → HCID 28378191, compound

HRID 1256666Notes

Reaction equation

HRID 1256666 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Cl[C:13]([O:15][CH3:16])=[O:14].CC(N(C)C)=O>O1CCOCC1>[C:13]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 31374DimethylacetamideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 28378191HCID 28378191, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To suspension of the 4-aminomethylbenzoic acid (10 g, 66.2 mmol) in 1,4-dioxane (100 mL) were added methyl chloroformate (5.4 mL, 69.5 mmol) and dimethyl acetamide (3.4 mL). The reaction mixture was then heated to 65° C. overnight. Reaction mixture was evaporated to dryness and the residue was triturated with water. The solids were filtered and dried to give pure product as white solid. 1H NMR (600 MHz, DMSO) δ 12.84 (bs, 1H), 7.85 (d, J=7.8 Hz, 2H), 7.73 (t, J=6 Hz, 1H), 7.32 (d, J=7.8 Hz, 2H), 4.20 (bd, J=6 Hz, 2H), 3.52 (s, 3H); MS: (MH+), (MH+).

Workup

  1. customReaction mixture
  2. customwas evaporated to dryness
  3. customthe residue was triturated with water
  4. filtrationThe solids were filtered
  5. customdried
  6. customto give pure product as white solid

Sources & evidence

ORD record
ord-8de507511ab84824bd38b9e2e553a5a8
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

Loading…