Ethyl isocyanate → 1-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

HRID 1399962Notes

Reaction equation

HRID 1399962 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Br:19])[C:12]2[S:16][C:15]([NH:17][C:23]([NH:22][CH2:20][CH3:21])=[O:24])=[N:14][C:13]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 578135885-(Benzyloxy)-7-bromobenzo[d]thiazol-2-amine

Product 1

HCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-ureaYield 75.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
82.5 °C

Procedure

To a suspension of vii (216 g, 0.64 mol) in 1,4-dioxane (4 L) was added ethylisocyanate (380 mL, 4.81 mol). The mixture was heated up to 80-85° C. overnight. The solvent was distilled off and the residue was co-evaporated with hexane. The residue was treated with H2O at 78-80° C. for 3-5 h. The resulting solid was filtered off and washed with hot H2O, dried under high vacuum to obtain viii (196 g, 75%). 1H-NMR (DMSO-d6, 400 MHz): δ 1.08 (t, J=7.20 Hz, 3H), 3.18 (q, J=6.80 Hz, 2H), 5.17 (s, 2H), 6.71 (br s, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.26 (br s, 1H), 7.31-7.47 (m, 5H) and 10.82 (br s, 1H). MS: 405.90 [M+H]+.

Workup

  1. distillationThe solvent was distilled off
  2. additionThe residue was treated with H2O at 78-80° C. for 3-5 h
  3. filtrationThe resulting solid was filtered off
  4. washwashed with hot H2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-3445797094c04f1faf766d8767b17e2c
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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