Diethyl Ether → 5-Chloro-N-{2-[3-(isocyanatomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

HRID 585512Notes

Reaction equation

HRID 585512 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[NH:17][C:18]([C:20]2[S:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[O:19])[C:8]1=[O:26].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[O:46]=[C:47](Cl)OC(Cl)(Cl)Cl.CCOCC>ClCCl>[Cl:25][C:22]1[S:21][C:20]([C:18]([NH:17][C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:14]=2[C:15](=[O:16])[N:7]([CH2:6][C:5]2[CH:27]=[CH:28][CH:29]=[C:3]([CH2:2][N:1]=[C:47]=[O:46])[CH:4]=2)[C:8]3=[O:26])=[O:19])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10426DiphosgeneHCID 88675Proton spongeHCID 22337012N-{2-[3-(Aminomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-5-chloro-2-thiophenecarboxamide

Product 1

HCID 223370985-Chloro-N-{2-[3-(isocyanatomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 430 mg (1.0 mmol) of N-{2-[3-(aminomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-5-chloro-2-thiophenecarboxamide and 433 mg (2.0 mmol) of 1,8-bis-(dimethylamino)naphthalene in 222 ml of dichloromethane is added dropwise to an ice-cooled solution of 0.12 ml (0.96 mmol) of diphosgene in 7.5 ml of dichloromethane. After 5 min at 0° C., the mixture is warmed to room temperature and stirred for 35 min, and 40 ml of ether are then added. Insoluble particles are filtered off and the filtrate is concentrated and dried under high vacuum. The resulting solid is immediately reacted further, without further purification. Yield: 454 mg (99.5% of theory).

Workup

  1. filtrationInsoluble particles are filtered off
  2. concentrationthe filtrate is concentrated
  3. customdried under high vacuum
  4. customThe resulting solid is immediately reacted further, without further purification

Sources & evidence

ORD record
ord-bd903072394e4117999b6197a8def1be
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

Loading…