Hydrochloric Acid → HCID 20215696, compound

HRID 236515Notes

Reaction equation

HRID 236515 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[CH2:24]([N:28]=[C:29]=[O:30])[CH2:25][CH2:26][CH3:27].Cl>C(C(C)=O)C>[CH2:24]([NH:28][C:29]([NH:17][S:14]([C:3]1[C:4]([S:8]([N:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:16])=[O:15])=[O:30])[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 14774740HCID 14774740, compound

Product 1

HCID 20215696HCID 20215696, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 140 mL of methyl ethyl ketone was added 14.3 g of 3-chloro-N,N-dimethyl-1,2-benzenedisulfonamide, 7.2 g of potassium carbonate and 7.5 ml of n-butyl isocyanate. This mixture was heated at reflux temperature for 3 hours, cooled to room temperature, poured into 1500 mL of ice water, and acidified to pH 1 with concentrated hydrochloric acid. The resulting precipitate was collected, washed with water, and dried to afford 17.4 g of N'-butylaminocarbonyl-3-chloro-N,N-dimethyl-1,2-benzenedisulfonamide as a white powder, m.p. 107°-115° C.; NMR (CDCl3): δ0.9 (br t, 3H), 1.2-1.7 (m, 4H), 3.0 (s, 6H), 3.3-3.4 (m, 2H), 6.6 (t, 1H), 7.6-8.0 (m, 2H), 8.5 (dd, 1H), 9.0 (br s, 1H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a03d04f283604985a697b95fae5b3697
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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