Ammonia → HCID 178421816, compound

HRID 1295068Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:13][N:12]=[C:11]2[C:7]=1[CH2:8][CH:9]1[C:14]([CH3:16])([CH3:15])[CH:10]12)=O)C.[NH3:17]>>[CH3:15][C:14]1([CH3:16])[CH:9]2[CH2:8][C:7]3[C:11]([CH:10]12)=[N:12][NH:13][C:6]=3[C:4]([NH2:17])=[O:3]

Participants

Reactant 2

HCID 222Ammonia

HCID 178470406HCID 178470406, compound

Product 1

HCID 178421816HCID 178421816, compound

Conditions

Temperature: 100 °C

Procedure

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (1.280 g, 5.81 mmol) was taken up in 7M methanolic ammonia (60 mL) in a sealed flask and heated to 100° C. for 18 hours. The resulting suspension was collected by vacuum filtration to give 1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide as a cream solid. Solvent was removed from the mother liquor and the residue purified by preparative HPLC to give further (±)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide as a cream solid. m/z (ES+): 192 [M+H]+, 175 [M−NH2]+; 1H NMR (CD3OD): δ 2.9–2.65 (m, 1H), 2.55 (t, 1H, J=19.9), 2.0–1.8 (m, 2H), 1.03 (s, 3H), 0.63 (s, 3H).

Workup

filtrationThe resulting suspension was collected by vacuum filtration

Sources & evidence

ORD record: ord-205c0052f0254696a9519a368b9ad3c2
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241792B2

Reaction notes

Loading…