Butyl isocyanate → 2-[[[(n-Butyl)aminocarbonyl]aminosulfonyl]methyl]-3-(N,N-dimethylamino)sulfonylbenzoic acid, methyl ester

HRID 2118431Notes

Reaction equation

HRID 2118431 reaction equation
[CH3:1][N:2]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[C:8]=1[CH2:17][S:18]([NH2:21])(=[O:20])=[O:19])(=[O:6])=[O:5])[CH3:3].[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:22]([NH:26][C:27]([NH:21][S:18]([CH2:17][C:8]1[C:7]([S:4]([N:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])=[CH:12][CH:11]=[CH:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14])(=[O:19])=[O:20])=[O:28])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 13937644HCID 13937644, compound

Product 1

HCID 139376452-[[[(n-Butyl)aminocarbonyl]aminosulfonyl]methyl]-3-(N,N-dimethylamino)sulfonylbenzoic acid, methyl esterYield 70.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 8.7 g of the product from Example 14, 2.7 g of n-butyl isocyanate, and 3.2 g anhydrous potassium carbonate in 75 ml methyl ethyl ketone was stirred at reflux temperature for 4.5 hours. The resulting suspension was then poured into 250 ml ice-water and the aqueous layer washed with diethyl ether. Concentrated hydrochloric acid was added to the water layer until a yellow solid formed. The crude product was collected by filtration, washed with n-butyl chloride and dried to give 7.9 g of the title compound as a pale yellow solid, m.p. 118°-134°; IR(nujol): 3400, 1725, 1700 cm-1 ; NMR (CDCl3): δ 0.8-1.6 (7H, m), 2.85 (6H, s, SO2N(CH3)2), 3.0 (2H, q), 3.95 (3H, s, CO2CH3), 5.75 (2H, s, --CH2 --), 6.25 (1H, t, NH), 7.2-8.2 (4 H, m).

Workup

  1. temperatureat reflux temperature for 4.5 hours
  2. washthe aqueous layer washed with diethyl ether
  3. additionConcentrated hydrochloric acid was added to the water layer until a yellow solid
  4. customformed
  5. filtrationThe crude product was collected by filtration
  6. washwashed with n-butyl chloride
  7. customdried

Sources & evidence

ORD record
ord-eed57093b80847fd882d76af9e695e02
Source dataset
uspto-grants-1987_07
Patent number
US04678500

Reaction notes

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