(Isocyanoimino)triphenylphosphorane → 8-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1848991Notes

Reaction equation

HRID 1848991 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14](O)=[O:15])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.[N+:19]([N:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[C-:20]>C1COCC1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[O:15][CH:20]=[N:19][N:21]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 11266621(Isocyanoimino)triphenylphosphoraneHCID 579001668-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylic acid

Product 1

HCID 579001858-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (22.2 g, 68.1 mmol) in THF (360 mL) was added (isocyanoimino)triphenylphosphorane (20.6 g, 68.1 mmol) portionwise over 1 hour. The resultant mixture was stirred at RT for 18 hours before being concentrated in vacuo and triturated with 1:1 DCM/cyclohexane (200 mL). The title compound was collected by filtration as a yellow solid (14.5 g, 61%). LCMS: RT=4.03 min, M+H+=350/352.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customtriturated with 1:1 DCM/cyclohexane (200 mL)
  3. filtrationThe title compound was collected by filtration as a yellow solid (14.5 g, 61%)

Sources & evidence

ORD record
ord-dfa467f2bfeb43ce88398335aa3a6afa
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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