Butyl isocyanate → HCID 13937615, compound

HRID 2118423Notes

Reaction equation

HRID 2118423 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:14][S:15]([NH2:18])(=[O:17])=[O:16])=[O:4].[CH2:19]([N:23]=[C:24]=[O:25])[CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:19]([NH:23][C:24]([NH:18][S:15]([CH2:14][C:6]1[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]([O:2][CH3:1])=[O:4])(=[O:17])=[O:16])=[O:25])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 13937614HCID 13937614, compound

Product 1

HCID 13937615HCID 13937615, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 7.7 g of the product from Example 4, 3.5 g of n-butyl isocyanate, and 4.8 g anhydrous potassium carbonate in 100 ml of methyl ethyl ketone was stirred at reflux temperature for 4 hours. After cooling to room temperature, the reaction mixture was concentrated to approximately one-third volume and diluted with 150 ml of water. The resulting solid was collected by filtration and washed with one portion of water and one portion of n-butyl chloride. The yield of N-[(n-butyl)aminocarbonyl]-2-(methoxycarbonyl)-6-nitrophenylmethanesulfonamide, m.p. 144°-150°, was 9.1 g as a tan solid; IR(nujol): 1725, 1665 cm-1, NMR (CDCl3 /DMSO-d6): δ 0.6-1.7 (7H, m), 2.9-3.4 (2H, m), 4.0 (3H, s, CO2CH3), 5.7 (2H, s, --CH2 --), 7.4-8.3 (3H, m), 10.5 (1H, br s, NH).

Workup

  1. temperatureat reflux temperature for 4 hours
  2. concentrationthe reaction mixture was concentrated to approximately one-third volume
  3. additiondiluted with 150 ml of water
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with one portion of water and one portion of n-butyl chloride

Sources & evidence

ORD record
ord-896241b0e47645f4adde7c9a6b922863
Source dataset
uspto-grants-1987_07
Patent number
US04678500

Reaction notes

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