2-(chloromethyl)-N,N-dimethylaniline → HCID 14064662, compound

HRID 1071550Notes

Reaction equation

HRID 1071550 reaction equation
Cl.[NH2:2][C:3]1[C:12](CCl)=[CH:11][CH:10]=[CH:9][C:4]=1C(OC)=O.[NH2:15][C:16]1[C:25]([CH2:26][S:27]([CH3:29])=O)=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].ClCC1C=CC=CC=1[N:34](C)C>C(O)(C)C>[NH2:15][C:16]1[C:25]([CH2:26][S:27][C:29]2[NH:2][C:3]3[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=3[N:34]=2)=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 107734552-(chloromethyl)-N,N-dimethylanilineHCID 13350297HCID 13350297, compoundHCID 13350307Methyl 2-amino-3-(chloromethyl)benzoate--hydrogen chloride (1/1)

Product 1

HCID 14064662HCID 14064662, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Example 1 using 1.27 g of methyl 2-amino-3-(chloromethyl)benzoate hydrochloride (prepared from methyl 2-amino-3-(methylsulfinylmethyl)benzoate as reported by J. P. Chupp et al., J. Org. Chem., 49, 4711 (1984) instead of 2-(chloromethyl)-N,N-dimethylaniline in isopropyl alcohol. Recrystallization of the title compound from diethyl ether gave 1.72 g of the title compound in three crops. Analysis. Calc'd. for C16H15N3O2S: C, 61.32; H, 4.82; N,13.41; S, 10.23. Found: C, 60.73; H, 4.86; N, 12.87; S, 9.67.

Workup

  1. customRecrystallization of the title compound from diethyl ether

Sources & evidence

ORD record
ord-e072c6e710a742d3be948783e0e5810f
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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