Ethanesulfonyl chloride → HCID 20061013, compound

HRID 1085131Notes

Reaction equation

HRID 1085131 reaction equation
[NH2:1][C:2]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[C:27]5[CH:26]=[CH:25][N:24]=[CH:23][C:22]=5[N:21]=[C:20]4[CH3:28])=[CH:15][CH:14]=3)[CH2:9][C:8](=[O:29])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>N1C=CC=CC=1>[CH2:30]([S:32]([NH:1][C:2]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[C:27]5[CH:26]=[CH:25][N:24]=[CH:23][C:22]=5[N:21]=[C:20]4[CH3:28])=[CH:15][CH:14]=3)[CH2:9][C:8](=[O:29])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:34])=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 20061015HCID 20061015, compound

Product 1

HCID 20061013HCID 20061013, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of the aniline from example 14 (0.5 g, 1.3 mmol) in dry pyridine (3 ml) was treated with ethanesulphonyl chloride (0.133 ml, 1.4 mmol). After 1 h, the mixture was evaporated to dryness then partitioned between dichloromethane and dilute aqueous sodium bicarbonate. The organic phase was dried over magnesium sulphate and evaporated to a yellow solid which was recrystallised from ethyl acetate (0.37 g, 59%). M.p. 258°-260° C.

Workup

  1. customthe mixture was evaporated to dryness
  2. customthen partitioned between dichloromethane and dilute aqueous sodium bicarbonate
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated to a yellow solid which
  5. customwas recrystallised from ethyl acetate (0.37 g, 59%)

Sources & evidence

ORD record
ord-cc3fbe84a8cb49f3af797ed6600be5b1
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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