1-Butanol → Tert-butyl (4-iodo-2-nitrophenyl)carbamate

HRID 859250Notes

Reaction equation

HRID 859250 reaction equation
[N-]=[C:2]=O.[I:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.[O:15]=[C:16](Cl)[O:17]C(Cl)(Cl)Cl.C(O)[CH2:24][CH2:25][CH3:26]>CCOC(C)=O.C(Cl)Cl>[C:25]([O:17][C:16](=[O:15])[NH:9][C:8]1[CH:10]=[CH:11][C:5]([I:4])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13])([CH3:24])([CH3:26])[CH3:2]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 10426DiphosgeneHCID 105034IsocyanateHCID 113690724-Iodo-2-nitroaniline

Product 1

HCID 23554339Tert-butyl (4-iodo-2-nitrophenyl)carbamateYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared the isocyanate from 4-iodo-2-nitroaniline (12.0 g, 45.5 mmol; prepared from 2-nitroaniline according to Wilson, J. Gerald; Hunt, Frederick C. Aust. J. Chem. 1983, 36, 2317–25; CAS-No. [20691-72-9]) with diphosgene (4.1 mL, 34.1 mmol) in EtOAc (250 mL), followed by treatment with tert.-BuOH (12 mL) in CH2Cl2 (60 mL) according to the general procedure A (method a). Obtained as a yellow solid (8.23 g, 82%). MS (EI) 390 (M+); mp 92–94° C.

Sources & evidence

ORD record
ord-d3ad7cfd223a4d95b3802d9144e746c8
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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