Acetyl chloride → HCID 21993065, compound

HRID 1979106Notes

Reaction equation

HRID 1979106 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([NH:9][S:10]([C:13]1[CH:18]=[C:17](N)[CH:16]=[C:15](C)[C:14]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:12])=[O:11])([CH3:8])([CH3:7])[CH3:6].[CH2:25]([N:27](CC)CC)C>ClCCl>[C:5]([NH:9][S:10]([C:13]1[CH:18]=[C:17]([CH2:25][NH:27][C:1](=[O:3])[CH3:2])[CH:16]=[CH:15][C:14]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:11])=[O:12])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70232061HCID 70232061, compound

Product 1

HCID 21993065HCID 21993065, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.63 g (8 mmol) of acetyl chloride dissolved in 10 ml of dichloromethane is added dropwise to a solution, cooled to 0° C., of 2.01 g (6.7 mmol) of N-tert-butyl-5-amino-methyl-2-methoxycarbonylbenzenesulfonamide and 0.93 ml (6.7 mmol) of triethylamine in 30 ml of dichloromethane, and the mixture is then stirred at room temperature for 2 h. The reaction solution is washed with water, dried and evaporated to dryness i.v. 2.1 g (91%) of N-tert-butyl-5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide are obtained as a viscous oil.   1 ⁢ H ⁢   ⁢ NMR ⁢   ⁢ ( 100 ⁢   ⁢ MHz , CDCl 3 ) ⁢ : ⁢   ⁢ δ =   ⁢ 1.25 ⁢   ⁢ ( s , 9 ⁢ H , C ⁡ ( CH 3 ) 3 ) ,   ⁢ 2.05 ⁢   ⁢ ( s , 3 ⁢ H , COCH 3 ) ,   ⁢ 3.95 ⁢   ⁢ ( s , 3 ⁢ H , OCH 3 ) ,   ⁢ 4.50 ⁢   ⁢ ( s , 2 ⁢ H , Ar— ⁢ CH 2 ) ,   ⁢ 6.15 ⁢   ⁢ ( s , 1 ⁢ H , SO 2 ⁢ NH ) ,   ⁢ 6.38 ⁢   ⁢ ( bt , 1 ⁢ H , NH ) ,   ⁢ 7.47 ⁢   ⁢ ( dd , 1 ⁢ H , Ar ⁢ — ⁢ H ) ,   ⁢ 7.75 ⁢   ⁢ ( d , 1 ⁢ H , Ar ⁢ —H ) ,   ⁢ 7.95 ⁢   ⁢ ( dd , 1 ⁢ H , Ar ⁢ — ⁢ H ) .

Workup

  1. additionis added dropwise to a solution
  2. washThe reaction solution is washed with water
  3. customdried
  4. customevaporated to dryness i.v

Sources & evidence

ORD record
ord-05e1c09d01914401935097fdabe6b273
Source dataset
uspto-grants-2001_05
Patent number
US06239306B1

Reaction notes

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