Chloroacetyl chloride → 5-t-butyl-2-methoxy-3-(chloroacetamido) phenyl N-t-butylsulfonamide

HRID 1651477Notes

Reaction equation

HRID 1651477 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]([C:10]1[CH:11]=[C:12]([NH2:26])[C:13]([O:24][CH3:25])=[C:14]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17])[CH:15]=1)([CH3:9])([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C>ClCCl>[C:6]([C:10]1[CH:11]=[C:12]([NH:26][C:3](=[O:4])[CH2:2][Cl:1])[C:13]([O:24][CH3:25])=[C:14]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:17])=[O:18])[CH:15]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 150295865-t-butyl-2-methoxy-3-aminophenyl N-t-butyl sulfonamide

Product 1

HCID 150295875-t-butyl-2-methoxy-3-(chloroacetamido) phenyl N-t-butylsulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloroacetyl chloride (4.4 ml) in dichloromethane (40 ml) was added dropwise to a cooled and stirred solution of 5-t-butyl-2-methoxy-3-aminophenyl N-t-butyl-sulfonamide (15.6 g) and diisopropylethylamine (9.5 ml) in dichloromethane (100 ml). The solution was left standing at ambient temperature for 2 hours and then washed with a 2% solution of citric acid. The organic phase was dried and evaporated. Recrytallization from aqueous ethanol gave the title compound (16.4 g).

Workup

  1. temperaturea cooled
  2. waitThe solution was left
  3. washwashed with a 2% solution of citric acid
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-979e8240d54b4415a395bd82d5be5d51
Source dataset
uspto-grants-1990_05
Patent number
US04929269

Reaction notes

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