2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1) → HCID 58055096, compound

HRID 1020251Notes

Reaction equation

HRID 1020251 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:14][N:15]=[C:16]=[O:17].CCN(C(C)C)C(C)C>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:14][NH:15][C:16]([NH:9][C:6]1[S:7][CH:8]=[C:4]([CH2:3][Cl:2])[N:5]=1)=[O:17]

Participants

5

Reactant 3

HCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzene

Product 1

HCID 58055096HCID 58055096, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-(chloromethyl)thiazol-2-amine hydrochloride (7.55 g, 41 mmol) in dichloromethane (150 mL) at 0° C. was added 3,4-dichlorobenzyl isocyanate (8.27 g, 41 mmol). A solution of DIPEA in dichloromethane (30 mL) was added over a period of 30 min and the mixture was stirred overnight at room temperature. Evaporation of the volatiles in vacuo followed by purification by column chromatography (EtOAc/heptane 1/1) afforded 1-(3,4-dichlorobenzyl)-3-(4-(chloromethyl)thiazol-2-yl)urea as an off-white solid (10.5 g, 30 mmol) in 73% yield. 1H-NMR (ppm, DMSO-d6): 10.80 (bs, 1H), 7.60 (d, 1H), 7.55 (s, 1H), 7.11 (t, 1H), 7.05 (s, 1H), 4.63 (s, 2H), 4.30 (d, 2H).

Workup

  1. customEvaporation of the volatiles in vacuo
  2. customfollowed by purification by column chromatography (EtOAc/heptane 1/1)

Sources & evidence

ORD record
ord-642e0cae361d499caad90aa5169f5e5b
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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