Methylamine → tert-Butyl (4-((methylamino)methyl)thiazol-2-yl)carbamate

HRID 1685019Notes

Reaction equation

HRID 1685019 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=1.O1CCCC1.[CH3:21][NH2:22]>>[CH3:21][NH:22][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 45117840tert-Butyl (4-(chloromethyl)thiazol-2-yl)carbamate

Product 1

HCID 58055063tert-Butyl (4-((methylamino)methyl)thiazol-2-yl)carbamate

Conditions

Temperature
60 °C

Procedure

tert-Butyl 4-(chloromethyl)thiazol-2-ylcarbamate (8.0 g, 24.16 mmol) was dissolved in 2.0 M methylamine in tetrahydrofuran (640 mL, ˜40 eq.) and heated in the microwave for 60 minutes at 60° C. The precipitate (impurity) was filtered off and the filtrate was concentrated under reduced pressure to furnish 1.97 g product as orange foam. 1H NMR (DMSO-d6): δ 11.79 (s, br, 1H), 7.50 (s, 1H), 7.36 (d, 1H), 7.10 (m, 2H), 5.14 (s, br, 1H), 4.63 (s, 2H), 4.36 (s, 2H), 3.83 (t, 2H), 3.43 (t, 2H).

Workup

  1. filtrationThe precipitate (impurity) was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8edd28c15b5346c0aa95a6294cc54d91
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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