Isothiocyanic acid, o-chlorobenzyl ester → HCID 178497000, compound

HRID 1898337Notes

Reaction equation

HRID 1898337 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[NH2:17].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][N:26]=[C:27]=S>C(#N)C>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][NH:26][C:27]1[NH:1][C:2]2[C:7]3[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=3[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=2[N:17]=1

Participants

4

Reactant 2

HCID 29351Isothiocyanic acid, o-chlorobenzyl esterHCID 67503724Methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate

Product 1

HCID 178497000HCID 178497000, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared following the procedure described for Step-1 of Intermediate-3 using methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate (Intermediate-1, 2.5 g, 10.59 mmol), 1-chloro-2-(isothiocyanatomethyl)benzene (2.5 g, 13.6 mmol), N,N-di-isopropyl carbodimide (0.5 mL) and acetonitrile (10.0 mL) to afford 2.00 g of the desired product. 1HNMR (DMSO-d6): δ 1.41 (s, 6H), 3.00 (s, 2H), 3.71 (s, 3H), 4.60 (d, J=5.3 Hz, 2H), 7.30-7.45 (m, 5H), 7.55 (t, J=6.6 Hz), 10.80 (s, 1H); MS [M+H]+: 386.05.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9a54e1d4fb47436a9f89f9c0a345942e
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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