Ethyl isocyanate → HCID 20551275, compound

HRID 1447292Notes

Reaction equation

HRID 1447292 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].C(N(CC)CC)C>CN(C)C=O>[CH2:18]([NH:20][C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 20551275HCID 20551275, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 9.2 g (40 mmol) of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 100 ml of dimethylformamide, 4.8 ml (60 mmol) of ethyl isocyanate and 5.6 ml (40 mmol) of triethylamine is stirred at 25° for 16 hrs. The dimethylformamide is evaporated under reduced pressure and the residue is treated with 200 ml of water and the pH is adjusted to 2.0 with 1 N hydrochloric acid. The solid is filtered and washed with methanol, ether and dried to give 11.8 g of 6-[4-(N-ethylcarbamoylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.

Workup

  1. customThe dimethylformamide is evaporated under reduced pressure
  2. additionthe residue is treated with 200 ml of water
  3. filtrationThe solid is filtered
  4. washwashed with methanol, ether
  5. customdried

Sources & evidence

ORD record
ord-103195b40fe64d03bb21205c8f08d4eb
Source dataset
uspto-grants-1982_02
Patent number
US04315858

Reaction notes

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