Ammonia → Methyl 3-carbamoyl-5-chlorobenzoate

HRID 1432063Notes

Reaction equation

HRID 1432063 reaction equation
[N:1]#N.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:12]=1)[C:7](O)=[O:8].S(Cl)(Cl)=O.N.O1CCOCC1>>[C:7]([C:6]1[CH:10]=[C:11]([CH:12]=[C:4]([Cl:3])[CH:5]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[NH2:1]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 947NitrogenHCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 247289213-Chloro-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

Procedure

Steps N2 and N3. A mixture of 3-chloro-5-(methoxycarbonyl)benzoic acid (2 g, 9.3 mmol) and thionyl chloride (8 mL) was refluxed for 2 hours. After the excess thionyl chloride was removed under vacuum, the residue was treated with a 0.5M solution of ammonia in 1,4-dioxane (40 mL, 20 mmol) overnight. The solvent was removed under vacuum and methyl 3-carbamoyl-5-chlorobenzoate was obtained as a white solid.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter the excess thionyl chloride was removed under vacuum
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d90479b6180248789395066f978a2974
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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