Dicyclohexylcarbodiimide → HCID 178436454, compound

HRID 614813Notes

Reaction equation

[C:1]([C:4]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]=1[OH:15])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1>N1C=CC=CC=1>[C:1]([C:4]1[C:5]([OH:15])=[C:6]([CH:10]=[C:11]([CH2:13][CH3:14])[CH:12]=1)[C:7]([NH:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1)=[O:8])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 3-acetyl-5-ethylsalicylic acid (55.0 g) and N,N'-dicyclohexylcarbodiimide (60.1 g) in dry pyridine (550 ml) was stirred at 25° C. for one hour. Anhydrous 5-aminotetrazole (24.7 g) was then added to the mixture, and stirring was continued at 60° C. for 24 hours. The pyridine was removed in vacuo, and the residue was treated with aqeuous ammonia solution (2N; 500 ml). The resulting slurry was stirred at between 90° and 100° C. for 15 minutes. The insoluble N,N'-dicyclohexylurea was filtered off, and the filtrate was acidified by treatment with concentrated hydrochloric acid. The resulting green precipitate was filtered off and recrystallized twice from aqueous dimethylformamide to give 3-acetyl-5-ethyl-2-hydroxy-N-(tetrazol-5-yl)benzamide (35.4 g), in the form of a pale yellow solid, m.p. 257°-258° C.

Workup

stirringstirring
waitwas continued at 60° C. for 24 hours
customThe pyridine was removed in vacuo
additionthe residue was treated with aqeuous ammonia solution (2N; 500 ml)
stirringThe resulting slurry was stirred at between 90° and 100° C. for 15 minutes
filtrationThe insoluble N,N'-dicyclohexylurea was filtered off
filtrationThe resulting green precipitate was filtered off
customrecrystallized twice from aqueous dimethylformamide

Sources & evidence

ORD record: ord-ee3e86adda7e4046ad339d953e247156
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146631

Reaction notes

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