1,1'-(Diazomethylene)bis(benzene) → HCID 54065091, compound

HRID 1284579Notes

Reaction equation

HRID 1284579 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:10]1[N:14]=[C:13]([NH2:15])[S:12][N:11]=1)[C:7]([OH:9])=[O:8])[CH:2]=[CH2:3].[C:16]1([C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N+]=[N-])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:1]([O:4][N:5]=[C:6]([C:10]1[N:14]=[C:13]([NH2:15])[S:12][N:11]=1)[C:7]([O:9][CH:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:8])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 54172645HCID 54172645, compound

Product 1

HCID 54065091HCID 54065091, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (10 g) in tetrahydrofuran (230 ml) was added portionwise diphenyldiazomethane (12.76 g) under cooling in an ice bath and stirring and the mixture was stirred for 2 hours at room temperature. The resulting mixture was concentrated under reduced pressure until an crystallization began and stood overnight at room temperature. The precipitates were collected by filtration, washed with ethyl acetate and dried to give diphenylmethyl 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (5.41 g), mp. 175° to 180° C. (dec.). The filtrate and the washings were combined and evaporated to dryness. The residue was crystallized from methylene chloride-diethyl ether (4:1) to give further crops of the object compound (6.7 g), which was recrystallized from acetonitrile.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. concentrationThe resulting mixture was concentrated under reduced pressure until an crystallization
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-99b3718755a8436298492bc7284a0815
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

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