Hydrochloric Acid → (4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 2250778Notes

Reaction equation

HRID 2250778 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1.N1C=CC=CC=1.Cl[C:20]([O:22][CH3:23])=[O:21].Cl>ClCCl>[CH3:23][O:22][C:20](=[O:21])[NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 6586Methyl chloroformate2×HCID 216224-Methoxy-2-aminobenzothiazole

Product 1

HCID 21303403(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-methoxybenzothiazol (23.6 g, 131 mmol) and pyridine (12.6 ml, 157 mmol) in dichloromethane (230 ml) are slowly treated with methyl chloroformate (10.6 ml, 137 mmol) at 0° C. After 10 minutes, further methyl chloroformate (1.0 ml, 13 mmol) and pyridine (1.0 ml, 12 mmol) are added. After 10 minutes, the mixture is poured into 200 ml 1M aqueous hydrochloric acid, the organic layer is separated, diluted with dichloromethane (250 ml) and washed with brine (50 ml). The organic phase is dried and the solvent evaporated in vacuo. 31.0 g (99.4%) white solid. MS: m/e=238 (M+H+).

Workup

  1. waitAfter 10 minutes
  2. customthe organic layer is separated
  3. additiondiluted with dichloromethane (250 ml)
  4. washwashed with brine (50 ml)
  5. customThe organic phase is dried
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-78a92fe12d2447ff9dba3f20f5189744
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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