Dichloromethane → Benzoic acid, 4-chloro-3-[(2-chloro-4,4-dimethyl-1,3-dioxopentyl)amino]-, hexadecyl ester

HRID 1275520Notes

Reaction equation

HRID 1275520 reaction equation
[C:1]([C:5](=[O:36])[CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:14])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:38]>>[C:1]([C:5](=[O:36])[CH:6]([Cl:38])[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:14])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 15508756Benzoic acid, 4-chloro-3-[(4,4-dimethyl-1,3-dioxopentyl)amino]-, hexadecyl ester

Product 1

HCID 15476485Benzoic acid, 4-chloro-3-[(2-chloro-4,4-dimethyl-1,3-dioxopentyl)amino]-, hexadecyl esterYield 94.5%

Procedure

To a suspension of 52.22 g (0.1 mol) of hexadecyl 3-[3-t-butyl-3-oxopropanamido]-4-chlorobenzoate 1 in 350 mL of CH2Cl2 was added 13.52 g (0.1 mol) of SO2Cl2. The mixture was gently refluxed for one hr, then stirred at room temperature for 0.5 hr. The solvent was removed under vacuum to yield a solid that was washed with ligroin and dried. There was thus obtained 52.62 g (94.5% yield) of 2, which was used in the following step.

Workup

  1. temperatureThe mixture was gently refluxed for one hr
  2. customThe solvent was removed under vacuum
  3. customto yield a solid
  4. washthat was washed with ligroin
  5. customdried

Sources & evidence

ORD record
ord-467c38de5ac44aaba177219ed6074827
Source dataset
uspto-grants-2000_12
Patent number
US06162598

Reaction notes

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