Triethylamine → HCID 11241959, compound

HRID 1017245Notes

Reaction equation

HRID 1017245 reaction equation
C([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([Cl:16])[CH:6]=1)(=O)C.C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>ClCCl>[Cl:16][C:7]1[C:8]([C:9]([NH:33][CH:30]2[CH2:32][CH2:31]2)=[O:11])=[CH:12][C:13]([O:14][CH3:15])=[C:5]([OH:4])[CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69828CyclopropylamineHCID 11253594HCID 11253594, compound

Product 1

HCID 11241959HCID 11241959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-acetoxy-2-chloro-5-methoxybenzoic acid (8.6 g, 35.2 mmol) and triethylamine (8.9 g, 88 mmol) in dry dichloromethane (100 ml) was cooled to 0° C. and ethylchloroformate (7.6 g, 70 mmol) was added at such a rate that the temperature stayed below 5° C. After 1 h cyclopropylamine (6.0 g, 105 mmol) was added. After stirring overnight at room temperature the organic phase was washed with water (2×200 ml). Drying over magnesium sulfate was followed by reduction of the solvent volume to half. Petrol ether was added and the product was filtered off. Yield 570 mg, 6.7%, mp 214-216° C.

Workup

  1. customstayed below 5° C
  2. washwas washed with water (2×200 ml)
  3. dry with materialDrying over magnesium sulfate
  4. additionPetrol ether was added
  5. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-a2ed74491ab24186a5708dba30e4ba7d
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Reaction notes

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