Methanesulfonyl chloride → HCID 20448267, compound

HRID 1395634Notes

Reaction equation

HRID 1395634 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[NH2:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=1[NH:10][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 20448267HCID 20448267, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

4-Nitro-o-phenylenediamine (30.6 g; 0.2 mole) was nearly dissolved in pyridine (ca. 500 ml.) The mixture was chilled to 5° C. and methanesulfonyl chloride (22.8 g; 0.2 mole) was added dropwise, while stirring, at <10° C. After the addition, the solution was left stirring at the ice bath temperature for about one hour. The reaction solution was poured into ice cold water (~2 liter) and stirred while scratching vigorously. The product was filtered and dried to yield 28.8 g (62 percent) beige solid, m.p. 201° to 204° C.

Workup

  1. additionAfter the addition
  2. waitthe solution was left
  3. stirringstirred
  4. filtrationThe product was filtered
  5. customdried

Sources & evidence

ORD record
ord-36acb20fcaee41b8bb828f0b87f46e2d
Source dataset
uspto-grants-1980_05
Patent number
US04204993

Reaction notes

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