Triethylamine → alpha-(4-Methoxybenzoyl)-alpha-[1-(4-carboxyphenyl)-5-tetrazolylthio]-2-chloro-5-dodecyloxycarbonylacetanilide

HRID 1248959Notes

Reaction equation

HRID 1248959 reaction equation
Cl[C:2]([C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)([Cl:27])[C:3]([N:5]([C:12]([O:14][CH:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[C:38]([C:41]1[CH:46]=[CH:45][C:44]([N:47]2[C:51]([SH:52])=[N:50][N:49]=[N:48]2)=[CH:43][CH:42]=1)([OH:40])=[O:39].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]([C:2]([S:52][C:51]2[N:47]([C:44]3[CH:43]=[CH:42][C:41]([C:38]([OH:40])=[O:39])=[CH:46][CH:45]=3)[N:48]=[N:49][N:50]=2)([Cl:27])[C:3]([N:5]([C:12]([O:14][CH:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86741145HCID 86741145, compoundHCID 178524450HCID 178524450, compound

Product 1

HCID 86741146alpha-(4-Methoxybenzoyl)-alpha-[1-(4-carboxyphenyl)-5-tetrazolylthio]-2-chloro-5-dodecyloxycarbonylacetanilideYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

33 g of α-chloro-α-(4-methoxybenzoyl)-2-chloro-5-dodecyloxycarbonylacetanilide and 16 g of 1-(4-carboxyphenyl)-5-mercaptotetrazole were dispersed in 200 ml of chloroform to which was added dropwise 10 ml of triethylamine at room temperature over a period of about 30 minutes. After stirring for 3 hours the chloroform solution was washed with water and concentrated under reduced pressure. The residue was recrystallized from methanol to obtain 41.2 g of α-(4-methoxybenzoyl)-α-[1-(4-carboxyphenyl)-5-tetrazolylthio]-2-chloro-5-dodecyloxycarbonylacetanilide. Yield: 93%. Melting Point: 172° to 174° C.

Workup

  1. washwas washed with water
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-6fcad6eccd0d40518c24aeffb2ff0aa7
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Reaction notes

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