Chlorosulfonyl isocyanate → HCID 20240770, compound

HRID 1981259Notes

Reaction equation

HRID 1981259 reaction equation
NS([C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:6]=1C(OC)=O)(=O)=O.NS(C1C=C(C2C=CC=CC=2)C=CC=1[C:28]([O:30][CH3:31])=[O:29])(=O)=O.Cl[S:43]([N:46]=[C:47]=[O:48])(=[O:45])=[O:44]>ClC1C=CC=CC=1>[C:28]([C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:6]=1[S:43]([N:46]=[C:47]=[O:48])(=[O:45])=[O:44])([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 13456737HCID 13456737, compoundHCID 20240769HCID 20240769, compound

Product 1

HCID 20240770HCID 20240770, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 1.8 g of methyl 2-(aminosulfonyl)-4-phenoxybenzoate (prepared by methods analogous to the sulfonamide of Example 5) in 15 mL chlorobenzene was treated with 0.55 mL of chlorosulfonyl isocyanate at room temperature, then heated to 100° for ca. 2 hours. The dark mixture was then cooled, decanted from some tarry residue and evaporated under reduced pressure. The title compound was indicated by the presence of a band at 2240 cm-1 in the infrared spectrum (neat liquid). It was used without further purification.

Workup

  1. temperatureheated to 100° for ca. 2 hours
  2. temperatureThe dark mixture was then cooled
  3. customdecanted from some tarry residue
  4. customevaporated under reduced pressure
  5. customIt was used without further purification

Sources & evidence

ORD record
ord-0e42f0b369bc457690fc7c91d821400e
Source dataset
uspto-grants-1985_04
Patent number
US04514213

Reaction notes

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