Triethylamine → HCID 22152627, compound

HRID 1111445Notes

Reaction equation

HRID 1111445 reaction equation
ClC1C=CC(NN=CC)=CC=1N[S:13]([CH3:16])(=[O:15])=[O:14].ClC1C=CC([N+]([O-])=O)=CC=1N.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=1[NH:38][S:39]([CH3:42])(=[O:41])=[O:40].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=1[N:38]([S:13]([CH3:16])(=[O:15])=[O:14])[S:39]([CH3:42])(=[O:40])=[O:41]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 226912-Chloro-5-nitroanilineHCID 31297Methanesulfonyl chlorideHCID 3113421HCID 3113421, compoundHCID 67750925HCID 67750925, compound

Product 1

HCID 22152627HCID 22152627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To prepare the starting material, acetaldehyde 4-chloro-3-methylsulfonylaminophenylhydrazone, a mixture of 20.0 5 (116 mmoles) of 2-chloro-5-nitroaniline (compound 4, FIG. 1), 24.6 g (243 mmoles) of triethylamine and 100 ml of methylene chloride was cooled in an ice bath, and a solution of 27.8 g (243 mmols) of methylsulfonyl chloride in 20 ml of methylene chloride was added dropwise. When the addition was about half complete the ice bath was removed. After completion of the addition, the mixture was allowed to stand for an hour and then filtered to remove undesired salts. The filtrate was evaporated under reduced pressure to give a yellow solid which was washed with 100 ml of water; the filter cake was then mixed with 100 ml of ethanol and then filtered rapidly, and the resulting off-white solid was dried in vacuo to give 32.7 g of 2-chloro-5-nitro-1-bis(methylsulfonyl)amino-benzene. The latter was then mixed with 50 ml of ethanol; 8 g of NaOH in 20 ml of water was added slowly with stirring, after which the mixture was diluted with 300 ml of water followed by the addition of 45 ml of 6N HCl, yielding a precipitate which was collected by filtration and dried in vacuo to give 24.3 g of 2-chloro-5-nitro-1-methylsulfonylaminobenzene (compound 4, FIG. 1). The latter material was reduced with iron powder to form 17.7 g of 4-chloro-3-methylsulfonylaminoiline.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionWhen the addition
  3. customwas removed
  4. additionAfter completion of the addition
  5. waitto stand for an hour
  6. filtrationfiltered
  7. customto remove undesired salts
  8. customThe filtrate was evaporated under reduced pressure
  9. customto give a yellow solid which
  10. washwas washed with 100 ml of water
  11. additionthe filter cake was then mixed with 100 ml of ethanol
  12. filtrationfiltered rapidly
  13. customthe resulting off-white solid was dried in vacuo

Sources & evidence

ORD record
ord-36393e9d657a4910930effd0f5284d95
Source dataset
uspto-grants-1990_12
Patent number
US04980480

Reaction notes

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