Ethyl chloroformate → 4-Amino-5-chloro-N-(1,2-dimethyl-4-pyrazolidinyl)-2-methoxybenzamide

HRID 1706402Notes

Reaction equation

HRID 1706402 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.C(OC(Cl)=O)C.[NH2:20][CH:21]1[CH2:25][N:24]([CH3:26])[N:23]([CH3:27])[CH2:22]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:20][CH:21]2[CH2:25][N:24]([CH3:26])[N:23]([CH3:27])[CH2:22]2)=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 516892Sodium BicarbonateHCID 20226460HCID 20226460, compound

Product 1

HCID 137468954-Amino-5-chloro-N-(1,2-dimethyl-4-pyrazolidinyl)-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A stirred solution of equal molar amounts of 4-amino-5-chloro-2-methoxybenzoic acid and triethylamine in methylene chloride (0°-5° C.) was treated dropwise with a slight excess of ethylchlorocarbonate. After 1.0 hour a solution of 4-amino-1,2-dimethylpyrazolidine in methylene chloride was added and the mixture stirred for about two hours at room temperature. An aqueous solution of sodium bicarbonate was added to the reaction mixture, the organic phase separated and concentrated to give the product which melted at 169°-171° C.

Workup

  1. customthe organic phase separated
  2. concentrationconcentrated
  3. customto give the product which melted at 169°-171° C.

Sources & evidence

ORD record
ord-3c5d249143fd4f1c9337d8b5f5b44d4a
Source dataset
uspto-grants-1980_06
Patent number
US04207327

Reaction notes

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