Sulfuryl chloride → 2-{3-[3-(4-n-Butoxyphenyl)-2-chloro-3-oxopropanamido]-4-chlorophenylcarboxy}ethyl-3,5-di-t-butyl-4-hydroxybenzoate

HRID 845370Notes

Reaction equation

HRID 845370 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([C:10]1[CH:11]=[C:12]([CH:45]=[C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])[C:47]=1[OH:48])[C:13]([O:15][CH2:16][CH2:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([NH:28][C:29](=[O:44])[CH2:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:35][CH:34]=2)=[O:32])[CH:22]=1)=[O:19])=[O:14])([CH3:9])([CH3:8])[CH3:7]>ClCCl>[CH2:40]([O:39][C:36]1[CH:35]=[CH:34][C:33]([C:31](=[O:32])[CH:30]([Cl:4])[C:29]([NH:28][C:23]2[CH:22]=[C:21]([O:20][C:18]([CH2:17][CH2:16][O:15][C:13](=[O:14])[C:12]3[CH:11]=[C:10]([C:6]([CH3:7])([CH3:8])[CH3:9])[C:47]([OH:48])=[C:46]([C:49]([CH3:51])([CH3:50])[CH3:52])[CH:45]=3)=[O:19])[CH:26]=[CH:25][C:24]=2[Cl:27])=[O:44])=[CH:38][CH:37]=1)[CH2:41][CH2:42][CH3:43]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 867422642-{3-[3-(4-n-Butoxyphenyl)-3-oxopropanamido]-4-chlorophenylcarboxy}ethyl 3,5-di-t-butyl-4-hydroxybenzoate

Product 1

HCID 867422652-{3-[3-(4-n-Butoxyphenyl)-2-chloro-3-oxopropanamido]-4-chlorophenylcarboxy}ethyl-3,5-di-t-butyl-4-hydroxybenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sulphuryl chloride (4.9 g, 36.2 mmole) in dichloromethane (10 ml) was slowly added to a solution of the 4 equivalent coupler from (f) (24.1 g, 36.2 mmole) in dichloromethane (140 ml). After stirring at room temperature for 21 hours, the volatiles were removed by rotary evaporation. The product was isolated as a yellow oil (25.1 g, 99%) and was used in the next reaction without further purification.

Workup

  1. customthe volatiles were removed by rotary evaporation

Sources & evidence

ORD record
ord-35cc148ce80d4261bee75b277fbf1728
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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